(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 1684694Notes

Reaction equation

HRID 1684694 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C@@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@H:13]([OH:16])[CH:14]=O.[C:24]([NH:28][C:29]([C@@H:31]1[CH2:40][C@H:39]2[C@H:34]([CH2:35][CH2:36][CH2:37][CH2:38]2)[CH2:33][NH:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].C([BH3-])#N.[Na+]>C(O)(=O)C>[C:24]([NH:28][C:29]([C@@H:31]1[CH2:40][C@H:39]2[C@H:34]([CH2:35][CH2:36][CH2:37][CH2:38]2)[CH2:33][N:32]1[CH2:14][C@@H:13]([OH:16])[C@@H:12]([N:3]1[C:2](=[O:1])[C:10]2=[CH:9][CH:8]=[CH:7][CH:6]=[C:5]2[C:4]1=[O:11])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 454736(3S,4aS,8aS)-N-(tert-Butyl)decahydroisoquinoline-3-carboxamideHCID 5003444Sodium cyanoborohydrideHCID 86751005(2S,3S)-3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-2-hydroxy-4-phenylbutyraldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

309 mg of (2S,3S)3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)2-hydroxy-4-phenylbutyraldehyde and 238 mg of N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide are dissolved in 5 ml of acetic acid and treated portionwise with 120 mg of sodium cyanoborohydride. After completion of the reaction the mixture is concentrated to dryness, treated with 10 ml of water and extracted with methylene chloride. The extracts are dried and filtered, the filtrate is concentrated and the residue is purified on silica gel with methylene chloride/methanol (95:5). N-tert.Butyl-decahydro-2-[2(R)-hydroxy-4-phenyl-3(S)-phthalimidobutyl]-(4aS,8aS)-isoquinoline-3(S)-carboxamide is obtained.

Workup

  1. customAfter completion of the reaction the mixture
  2. concentrationis concentrated to dryness
  3. additiontreated with 10 ml of water
  4. extractionextracted with methylene chloride
  5. customThe extracts are dried
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated
  8. customthe residue is purified on silica gel with methylene chloride/methanol (95:5)

Sources & evidence

ORD record
ord-274b2ef47e6041999eceee98cbfe21ca
Source dataset
uspto-grants-1997_06
Patent number
US05641886

Reaction notes

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