(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 1940185ノート

反応式

HRID 1940185 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-df8c5f41a64843eeaeb329201d264e51
出典データセット
uspto-grants-1997_12
特許番号
US05698698

反応ノート

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