(3S,4aS,8aS)-N-(tert-Butyl)decahydroisoquinoline-3-carboxamide → N-tert.butyl-decahydro-2-[2(R)-hydroxy-4-phenyl-3(S)-phthalimidobutyl]-(4aS,8aS)-isoquinoline-3(S)-carboxamide

HRID 440103노트

반응식

HRID 440103 반응식
[C:1]1([CH2:7][C@@H:8]([C@H:20]2[CH2:22][O:21]2)[N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([NH:27][C:28]([C@@H:30]1[CH2:39][C@H:38]2[C@H:33]([CH2:34][CH2:35][CH2:36][CH2:37]2)[CH2:32][NH:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>CN(C)C=O>[C:23]([NH:27][C:28]([C@@H:30]1[CH2:39][C@H:38]2[C@H:33]([CH2:34][CH2:35][CH2:36][CH2:37]2)[CH2:32][N:31]1[CH2:22][C@@H:20]([OH:21])[C@@H:8]([N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

참가 물질

4

반응물 2

HCID 454736(3S,4aS,8aS)-N-(tert-Butyl)decahydroisoquinoline-3-carboxamideHCID 102663882(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane

생성물 1

HCID 9915000N-tert.butyl-decahydro-2-[2(R)-hydroxy-4-phenyl-3(S)-phthalimidobutyl]-(4aS,8aS)-isoquinoline-3(S)-carboxamide수율 59.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A stirred solution of 4.39 g (15 mmol) of 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane and 3.57 g (15 mmol) of N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide in 30 ml of dimethylformamide was heated at 120° C. for 10 hours and then left to stand at room temperature for 18 hours. The mixture was evaporated to dryness under reduced pressure. The residue was dissolved in 50 ml of ethyl acetate, washed with 30 ml of water, dried over anhydrous sodium sulphate, filtered and evaporated. The crude product was crystallized from ethyl acetate/n-hexane and there were obtained 4.77 g of N-tert.butyl-decahydro-2-[2(R)-hydroxy-4-phenyl-3(S)-phthalimidobutyl]-(4aS,8aS)-isoquinoline-3(S)-carboxamide in the form of a cream coloured solid; MS: m/e 532 [M+H]+.

후처리

  1. waitleft
  2. customThe mixture was evaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in 50 ml of ethyl acetate
  4. washwashed with 30 ml of water
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was crystallized from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-54ce362f7cdd4e7aabfdfddaaec78a22
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05516913

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