(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 440103Notes

Reaction equation

HRID 440103 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-54ce362f7cdd4e7aabfdfddaaec78a22
Source dataset
uspto-grants-1996_05
Patent number
US05516913

Reaction notes

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