常温常压下稳定,避免与强氧化剂接触。
N-Boc-4-羟基哌啶是合成多种生物活性化合物的重要中间体,如盐皮质激素受体拮抗剂的二氢苯并咪唑、用于治疗阿尔茨海默病M2毒蕈碱受体拮抗剂、Trk抑制剂的稠环杂芳基化合物以及新型吡唑并吡啶类抗肿瘤化合物。这些应用使得N-Boc-4-羟基哌啶在医药行业具有广泛的应用前景。
制备第一步:
将153.6克(1.0摩尔)4-哌啶酮水合盐酸盐和150.0克水加入到1升三口瓶中,控温20-30℃下滴加400.0克(2.0摩尔)20%氢氧化钠溶液。滴加完毕后搅拌20分钟,再滴加240.0克(1.1摩尔)二碳酸二叔丁酯((Boc)₂O),滴毕后在20-30℃下继续搅拌反应约12小时。通过TLC监测原料完全反应后,降温过滤,滤液保留待后续使用。粗品用乙醇重结晶并干燥,最终获得180.5克白色固体N-Boc-4-哌啶酮,GC含量为99.4%,收率为90.6%。
第二步:
在氮气保护下,将180.5克(0.906摩尔)N-Boc-4-哌啶酮、542克甲苯、55.5克异丙醇铝和653.0克异丙醇加入到2升三口瓶中,并加热至50℃搅拌24小时。GC监测原料完全反应后,降温,使用1N盐酸淬灭反应,进行甲苯萃取并合并有机层,用饱和氯化钠洗涤一次,减压浓缩溶剂。粗品通过正庚烷重结晶,真空干燥得156.3克白色固体N-Boc-4-羟基哌啶,GC含量为99.1%。
用途N-Boc-4-羟基哌啶可作为原料用于通过Mitsunobu反应合成N-杂环烷基醚。
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
1-Boc-哌啶 | t-butyl piperidinecarboxylate | 75844-69-8 | C10H19NO2 | 185.266 |
N-叔丁氧羰基-4-哌啶酮 | N-tert-butyloxycarbonylpiperidin-4-one | 79099-07-3 | C10H17NO3 | 199.25 |
1-Boc-4-氨基哌啶 | 1-(tert-butoxycarbonyl)-4-aminopiperidine | 87120-72-7 | C10H20N2O2 | 200.281 |
1-Boc-4-甲烷磺酰氧基哌啶 | 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate | 141699-59-4 | C11H21NO5S | 279.357 |
—— | tert-butyl 4-(3-chlorophenoxy)piperidine-1-carboxylate | 552868-09-4 | C16H22ClNO3 | 311.809 |
—— | tert-butyl 4-(4-benzyloxyphenoxy)piperidine-1-carboxylate | 254883-36-8 | C23H29NO4 | 383.488 |
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
4-甲氧基-1-哌啶羧酸叔丁酯 | tert-butyl 4-methoxypiperidine-1-carboxylate | 188622-27-7 | C11H21NO3 | 215.293 |
叔丁基 4-(氨基氧基)哌啶-1-羧酸 | tert-butyl 4-(aminooxy)piperidine-1-carboxylate | 867034-25-1 | C10H20N2O3 | 216.28 |
N-BOC-4-甲基-4-羟基哌啶 | tert-butyl 4-hydroxy-4-methylpiperidine-1-carboxylate | 406235-30-1 | C11H21NO3 | 215.293 |
N-BOC-4-乙氧基哌啶 | tert-butyl 4-ethoxypiperidine-1-carboxylate | 460367-82-2 | C12H23NO3 | 229.32 |
—— | tert-butyl 4-(2-aminoethoxy)piperidine-1-carboxylate | 442126-36-5 | C12H24N2O3 | 244.334 |
1-Boc-哌啶 | t-butyl piperidinecarboxylate | 75844-69-8 | C10H19NO2 | 185.266 |
—— | tert-butyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate | 163210-40-0 | C12H23NO4 | 245.319 |
4-(哌啶-4-基氧基)哌啶-1-羧酸叔丁酯 | tert-butyl 4-(piperidin-4-yloxy)piperidine-1-carboxylate | 845305-83-1 | C15H28N2O3 | 284.399 |
—— | tert-butyl 4-(allyloxy)piperidine-1-carboxylate | 163210-43-3 | C13H23NO3 | 241.331 |
—— | tert-butyl 4-(prop-2-yn-1-yloxy)piperidine-1-carboxylate | 1219827-56-1 | C13H21NO3 | 239.315 |
4-(2-氧代乙氧基)哌啶-1-羧酸叔丁酯 | tert-butyl 4-(2-oxoethoxy)piperidine-1-carboxylate | 919360-34-2 | C12H21NO4 | 243.303 |
—— | tert-butyl 4-(3-hydroxypropoxy)piperidine-1-carboxylate | 303975-37-3 | C13H25NO4 | 259.346 |
—— | 4-(3-methoxypropyloxy)-N-t-butyloxycarbonylpiperidine | 303975-39-5 | C14H27NO4 | 273.373 |
—— | tert-butyl 4-(2-methoxyethoxy)piperidine-1-carboxylate | 800401-96-1 | C13H25NO4 | 259.346 |
—— | 1-(tert-butoxycarbonyl)-4-[(2-cyanoethyl)oxy]piperidine | 190515-53-8 | C13H22N2O3 | 254.329 |
—— | 2-[(1-tert-butoxycarbonylpiperidine-4-yl)oxy]-N,N-dimethylethylamine | —— | C14H28N2O3 | 272.388 |
—— | 2-methylpropan-2-yl 4-(acetyloxy)piperidine-1-carboxylate | 850452-53-8 | C12H21NO4 | 243.303 |
—— | tert-butyl 4-(2-(2-methoxyethoxy)ethoxy)piperidin-1-carboxylate | —— | C15H29NO5 | 303.399 |
—— | tert-butyl 4-((chlorocarbonyl)oxy)piperidine-1-carboxylate | 1315192-00-7 | C11H18ClNO4 | 263.721 |
—— | tert-butyl 4-(2-morpholinoethoxy)piperidin-1-carboxylate | 1174044-47-3 | C16H30N2O4 | 314.425 |
—— | Tert-butyl 4-carbamothioyloxypiperidine-1-carboxylate | 871828-50-1 | C11H20N2O3S | 260.357 |
4-氨基甲酰基甲氧基哌啶-1-羧酸叔丁酯 | tert-butyl 4-(2-amino-2-oxoethoxy)piperidine-1-carboxylate | 857653-96-4 | C12H22N2O4 | 258.318 |
1-Boc-4-哌啶氧乙酸 | 4-(carboxymethoxy)piperidine-1-carboxylic acid tert-butyl ester | 161948-70-5 | C12H21NO5 | 259.302 |
—— | tert-butyl 4-(6-bromo-hexyloxy)-piperidine-1-carboxylate | 192437-77-7 | C16H30BrNO3 | 364.323 |
—— | 4-(2-carboxyethoxy)piperidine-1-carboxylic acid tert-butyl ester | 773099-94-8 | C13H23NO5 | 273.329 |
—— | tert-Butyl 4-(2,2,2-trifluoroethoxy)-1-piperidinecarboxylate | 442199-13-5 | C12H20F3NO3 | 283.291 |
N-叔丁氧羰基-4-哌啶酮 | N-tert-butyloxycarbonylpiperidin-4-one | 79099-07-3 | C10H17NO3 | 199.25 |
—— | tert-butyl 4-(3-methoxy-3-oxopropoxy)piperidine-1-carboxylate | 918967-70-1 | C14H25NO5 | 287.356 |
4-氯-N-Boc-哌啶 | tert-butyl 4-chloropiperidine-1-carboxylate | 154874-94-9 | C10H18ClNO2 | 219.711 |
2-氯-5-硝基烟酸乙酯 | tert-butyl 4-(2-methoxy-2-oxoethoxy)piperidine-1-carboxylate | 179689-21-5 | C13H23NO5 | 273.329 |
1-Boc-4-乙氧基羰基甲氧基哌啶 | tert-butyl 4-(2-ethoxy-2-oxoethoxy)piperidine-1-carboxylate | 189889-45-0 | C14H25NO5 | 287.356 |
—— | tert-butyl 4-(allyloxy)-4-methylpiperidine-1-carboxylate | 1551896-48-0 | C14H25NO3 | 255.357 |
4-溴-N-Boc-哌啶 | tert-butyl 4-bromo-1-piperidinecarboxylate | 180695-79-8 | C10H18BrNO2 | 264.162 |
4-氟哌啶-n-羧酸叔丁酯 | tert-butyl 4-fluoropiperidine-1-carboxylate | 178181-55-0 | C10H18FNO2 | 203.257 |
—— | tert-butyl 4-[2-(dimethylamino)-2-oxoethoxy]piperidine-1-carboxylate | 1165800-39-4 | C14H26N2O4 | 286.371 |
N-Boc-4-碘哌啶 | tert-butyl 4-iodopiperidine-1-carboxylate | 301673-14-3 | C10H18INO2 | 311.163 |
1-N-boc-4-疏基哌啶 | tert-butyl 4-mercapto-1-piperidinecarboxylate | 134464-79-2 | C10H19NO2S | 217.332 |
2-甲基-2-丙基4-烯丙基-1-哌啶羧酸酯 | tert-butyl 4-allylpiperidine-1-carboxylate | 206446-47-1 | C13H23NO2 | 225.331 |
2-甲基-2-丙基3,4-二羟基-1-哌啶羧酸酯 | tert-butyl 3,4-dihydroxypiperidine-1-carboxylate | 475062-48-7 | C10H19NO4 | 217.265 |
—— | tert-butyl 4-(((methylthio)carbonothioyl)oxy)piperidine-1-carboxylate | 1612172-49-2 | C12H21NO3S2 | 291.436 |
2-(1-(叔丁氧基羰基)哌啶-4-基氧基)丙酸 | 4-(1-carboxyethoxy)piperidine-1-carboxylic acid tert-butyl ester | 952486-65-6 | C13H23NO5 | 273.329 |
—— | (2S)-2-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]propanoic acid | 952486-63-4 | C13H23NO5 | 273.329 |
—— | (R)-2-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)propanoic acid | 952486-64-5 | C13H23NO5 | 273.329 |
—— | tert-butyl 4-(3-cyano-2-oxopropoxy)piperidine-1-carboxylate | 1424763-48-3 | C14H22N2O4 | 282.34 |
N-Boc-4-氰基哌啶 | 1-tert-butoxycarbonyl-4-cyanopiperidine | 91419-52-2 | C11H18N2O2 | 210.276 |
1-Boc-4-甲烷磺酰氧基哌啶 | 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate | 141699-59-4 | C11H21NO5S | 279.357 |
—— | 3-(1-(tert-butoxycarbonyl)piperidin-4-yl)oxy-3-oxopropanoic acid | 918641-95-9 | C13H21NO6 | 287.313 |
—— | 2(RS)-[2-(N-t-butoxycarbonyl-4-piperidyloxy)ethyl]piperidine | 441771-94-4 | C17H32N2O3 | 312.453 |
—— | tert-butyl 4-(2-oxo-2-(piperidin-1-yl)ethoxy)piperidine-1-carboxylate | 1174044-64-4 | C17H30N2O4 | 326.436 |
—— | tert-butyl 4-cyclopropylpiperidine-1-carboxylate | 208245-60-7 | C13H23NO2 | 225.331 |
—— | Tert-butyl 4-dimethoxyphosphoryloxypiperidine-1-carboxylate | 1195972-57-6 | C12H24NO6P | 309.299 |
4-(苄氧基)哌啶-1-羧酸叔丁酯 | 4-benzyloxypiperidine-1-carboxylic acid tert-butyl ester | 159557-47-8 | C17H25NO3 | 291.39 |
—— | tert-butyl 4-(2-oxo-2-(pyrrolidin-1-yl)ethoxy)piperidine-1-carboxylate | 1174044-60-0 | C16H28N2O4 | 312.409 |
4-(甲基硫代)哌啶-1-羧酸叔丁酯 | 1-tert-butoxycarbonyl-4-methylthiopiperidine | 208245-69-6 | C11H21NO2S | 231.359 |
—— | 1-(tert-butoxycarbonyl)piperidin-4-yl 4-isopropylpiperazine-1-carboxylate | 1542135-88-5 | C18H33N3O4 | 355.478 |
3-碘-氮杂丁烷-1-羧酸叔丁酯 | tert-butyl 4-phenoxypiperidine-1-carboxylate | 155989-69-8 | C16H23NO3 | 277.364 |
—— | Tert-butyl 4-(2-morpholino-2-oxoethoxy)piperidine-1-carboxylate | 1174044-46-2 | C16H28N2O5 | 328.409 |
—— | N-BOC-4-[(tetrahydropyran-2-yl)oxy]piperidine | 152491-44-6 | C15H27NO4 | 285.384 |
—— | N-tert-butoxycarbonyl-4-p-methylbenzyloxypiperidine | 1121633-93-9 | C18H27NO3 | 305.417 |
—— | 4-trifluoromethyl-piperidine-1-carboxylic acid tert-butyl ester | 623165-99-1 | C11H18F3NO2 | 253.265 |
1-Boc-3,4-环氧哌啶 | tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate | 161157-50-2 | C10H17NO3 | 199.25 |
—— | O2-[1-(tert-butoxycarbonyl)piperidin-4-yl]1-(N-tert-butylamino)diazen-1-ium-1,2-diolate | 1398743-46-8 | C14H28N4O4 | 316.401 |
—— | tert-butyl 4-(4-hydroxyphenoxy)piperidine-1-carboxylate | 681484-29-7 | C16H23NO4 | 293.363 |
4-叠氮基哌啶-1-羧酸叔丁酯 | tert-butyl 4-azidopiperidine-1-carboxylate | 180695-80-1 | C10H18N4O2 | 226.279 |
4-(嘧啶-2-基氧基)-哌啶-1-羧酸叔丁酯 | tert-butyl 4-(pyrimidin-2-yloxy)piperidine-1-carboxylate | 412293-91-5 | C14H21N3O3 | 279.339 |
4-(吡啶-4-基氧基)哌啶-1-羧酸叔丁酯 | tert-butyl 4-(pyridin-4-yloxy)piperidine-1-carboxylate | 308386-35-8 | C15H22N2O3 | 278.351 |
—— | 4-tert-butylamino-piperidine-1-carboxylic acid tert-butyl ester | 871828-36-3 | C14H28N2O2 | 256.389 |
—— | tert-butyl 4-[tert-butyl(dimethyl)silyl]oxypiperidine-1-carboxylate | 97231-88-4 | C16H33NO3Si | 315.528 |
(1-(叔丁氧基羰基)哌啶-4-基)硼酸 | (1-(tert-butoxycarbonyl)piperidin-4-yl)boronic acid | 1251537-39-9 | C10H20BNO4 | 229.084 |
—— | tert-butyl 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)piperidine-1-carboxylate | 863615-16-1 | C18H37NO4Si | 359.582 |
—— | tert-butyl 4-[6-(benzyloxy)hexyloxy]piperidine-1-carboxylate | 872692-32-5 | C23H37NO4 | 391.551 |
—— | 1-tert-butoxycarbonyl-4-(3-tert-butyldimethylsilyloxypropoxy)piperidine | 931097-60-8 | C19H39NO4Si | 373.608 |
4-(4-溴苄氧基)哌啶-1-羧酸叔丁酯 | tert-butyl 4-(4-bromobenzyloxy)piperidin-1-carboxylate | 930111-10-7 | C17H24BrNO3 | 370.286 |
4-[(乙氧基羰基)甲基]-4-羟基哌啶-1-羧酸叔丁酯 | tert-butyl 4-(2-ethoxy-2-oxoethyl)-4-hydroxypiperidine-1-carboxylate | 401811-97-0 | C14H25NO5 | 287.356 |
1-BOC-4-(4-溴苯氧基)哌啶 | tert-butyl 4-(4-bromophenoxy)piperidine-1-carboxylate | 308386-38-1 | C16H22BrNO3 | 356.26 |
4-(4-氯-苯氧基)-哌啶-1-羧酸叔丁酯 | tert-butyl 4-(4-chlorophenoxy)piperidine-1-carboxylate | 333954-83-9 | C16H22ClNO3 | 311.809 |
—— | tert-butyl 4-((4-fluorobenzyl)oxy)piperidine-1-carboxylate | 1121587-29-8 | C17H24FNO3 | 309.381 |
—— | tert-butyl 4-((4-cyanobenzyl)oxy)piperidine-1-carboxylate | 912947-06-9 | C18H24N2O3 | 316.4 |
—— | tert-butyl 4-(4-fluorophenoxy)piperidine-1-carboxylate | 333954-85-1 | C16H22FNO3 | 295.354 |
4-哌嗪四氢-1(2H)-吡啶羧酸叔丁酯 | tert-butyl 4-(piperazin-1-yl)piperidine-1-carboxylate | 177276-41-4 | C14H27N3O2 | 269.387 |
4-(4-氨基苯氧基)-1-哌啶甲酸叔丁酯 | tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate | 138227-63-1 | C16H24N2O3 | 292.378 |
—— | tert-butyl 4-(4-iodophenoxy)piperidine-1-carboxylate | 346617-98-9 | C16H22INO3 | 403.26 |
—— | tert-butyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)piperidine-1-carboxylate | 1029429-49-9 | C11H21NO4 | 231.292 |
1-Boc-4-二甲基氨基甲酰哌啶 | tert-butyl 4-(dimethylcarbamoyl)piperidine-1-carboxylate | 254905-58-3 | C13H24N2O3 | 256.345 |
4-(三氟甲基磺酰氧基)哌啶-1-羧酸叔丁酯 | tert-butyl 4-(((trifluoromethyl)sulfonyl)oxy)piperidine-1-carboxylate | 1138820-45-7 | C11H18F3NO5S | 333.329 |
—— | 4-(1-tert-butoxycarbonylpiperidin-4-yloxy)phenoxyacetic acid | 247133-55-7 | C18H25NO6 | 351.4 |
—— | tert-butyl 4-((5-aminopyrimidin-2-yl)oxy)piperidine-1-carboxylate | 862313-64-2 | C14H22N4O3 | 294.354 |
4-(乙酰硫基)哌啶-1-羧酸叔丁酯 | tert-butyl 4-(acetylthio)piperidine-1-carboxylate | 141699-66-3 | C12H21NO3S | 259.37 |
4-(5-溴嘧啶-2-氧基)哌啶-1-羧酸叔丁酯 | tert-butyl 4-((5-bromopyrimidin-2-yl)oxy)piperidine-1-carboxylate | 832735-41-8 | C14H20BrN3O3 | 358.235 |
4-(4-吗啉基)-1-哌啶羧酸叔丁酯 | tert-butyl 4-morpholinopiperidine-1-carboxylate | 125541-20-0 | C14H26N2O3 | 270.372 |
—— | tret-butyl 4-[(3-bromobenzyl)oxy]piperidine-1-carboxylate | 931410-04-7 | C17H24BrNO3 | 370.286 |
4-(4-甲酰基苯氧基)哌啶-1-羧酸叔丁酯 | tert-butyl 4-(4-formylphenoxy)piperidine-1-carboxylate | 207798-38-7 | C17H23NO4 | 305.374 |
—— | 1-(tert-butoxycarbonyl)-4-(3-fluorophenoxy)piperidine | 920511-29-1 | C16H22FNO3 | 295.354 |
4-(4-(三氟甲氧基)苯氧基)哌啶-1-羧酸叔丁酯 | 4-(4-(trifluoromethoxy)phenoxy)piperidine | 287952-66-3 | C17H22F3NO4 | 361.361 |
—— | 4-((S)-2-methyl-pyrrolidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester | 1228674-24-5 | C15H28N2O2 | 268.4 |
4-(4-(羟基甲基)苯氧基)哌啶-1-甲酸叔丁酯 | tert-butyl 4-[4-(hydroxymethyl)phenoxy]piperidine-1-carboxylate | 321337-38-6 | C17H25NO4 | 307.39 |
1-BOC-4-(3-溴苯氧基)哌啶 | tert-butyl 4-(3-bromophenoxy)piperidine-1-carboxylate | 790667-54-8 | C16H22BrNO3 | 356.26 |
4-(4-氰基苯氧基)哌啶-1-羧酸叔丁酯 | tert-butyl 4-(4-cyanophenoxy)piperidine-1-carboxylate | 333954-86-2 | C17H22N2O3 | 302.373 |
—— | tert-butyl 4-(3-chlorophenoxy)piperidine-1-carboxylate | 552868-09-4 | C16H22ClNO3 | 311.809 |
4-(3-氨基苯氧基)哌啶-1-羧酸叔丁酯 | tert-butyl 4-(3-aminophenoxy)piperidine-1-carboxylate | 790667-68-4 | C16H24N2O3 | 292.378 |