(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 1940185노트

반응식

HRID 1940185 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-df8c5f41a64843eeaeb329201d264e51
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05698698

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