1,1-Dimethylethyl (trans)-3-hydroxy4-[[(phenylmethyl)amino]methyl]-1-piperidinecarboxylate → trans-1-Boc-4-aminomethyl-3-hydroxypiperidine

HRID 353339

반응식

HRID 353339 반응식
[OH:1][C@H:2]1[C@H:7]([CH2:8][NH:9]CC2C=CC=CC=2)[CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1>CO.[Pd]>[NH2:9][CH2:8][C@@H:7]1[CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:3][C@H:2]1[OH:1]

참가 물질

4

반응물 1

HCID 117387271,1-Dimethylethyl (trans)-3-hydroxy4-[[(phenylmethyl)amino]methyl]-1-piperidinecarboxylate

생성물 1

HCID 11075229trans-1-Boc-4-aminomethyl-3-hydroxypiperidine수율 76%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of intermediate (1-d) (max. 0.023 mol crude residue) in methanol (100 ml) was hydrogenated with palladium-on-carbon (10%, 1 g) as a catalyst. After uptake of H2 (1 equivalent), the catalyst was filtered off and the filtrate was evaporated. The residue was solidified in DIPE+ACN, filtered off and dried (vacuum, 40° C.), yielding 4 g (76%) of 1,1-dimethylethyl (trans)-4-(aminomethyl)-3-hydroxy-1-piperidinecarboxylate (intermediate 1-e, mp. 178° C.). In an analogous way, but starting from cis-3-hydroxy-4-piperidinemethanol (described in J. Org. Chem., 34, pp. 3674-3676 (1969)), 1,1-dimethylethyl (cis)-4-(aminomethyl)-3-hydroxy-1-piperidinecarboxylate (interm. 1-f) was prepared.

후처리

  1. filtrationAfter uptake of H2 (1 equivalent), the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. filtrationfiltered off
  4. customdried (vacuum, 40° C.)

출처 및 근거

ORD 기록
ord-b8615269d4a34172a962559d6412d065
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06750349B2

연결된 노트

불러오는 중…