1-Benzothiophene-2-carbaldehyde → (2S,3aS,7aS)-2-{[(Benzo[b]thiophen-2-ylmethyl)-amino]-methyl}-octahydro-indole-1-carboxylic acid tert-butyl ester

HRID 2220714ノート

反応式

HRID 2220714 の反応式
[S:1]1[C:5]([CH:6]=O)=[CH:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[C:12]([O:16][C:17]([N:19]1[C@@H:27]2[C@@H:22]([CH2:23][CH2:24][CH2:25][CH2:26]2)[CH2:21][C@H:20]1[CH2:28][NH2:29])=[O:18])([CH3:15])([CH3:14])[CH3:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:12]([O:16][C:17]([N:19]1[C@@H:27]2[C@@H:22]([CH2:23][CH2:24][CH2:25][CH2:26]2)[CH2:21][C@H:20]1[CH2:28][NH:29][CH2:6][C:5]1[S:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[CH:4]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 7365001-Benzothiophene-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58622131tert-butyl (2S,3aS,7aS)-2-(aminomethyl)-octahydro-1H-indole-1-carboxylate

生成物 1

HCID 58622260(2S,3aS,7aS)-2-{[(Benzo[b]thiophen-2-ylmethyl)-amino]-methyl}-octahydro-indole-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Experimental conditions analogous to Example 1, from 0.1 g (0.63 mmol) of benzo[b]thiophene-2-carbaldehyde, 0.16 g (0.63 mmol) of (2S,3aS,7aS)-2-aminomethyl-octahydro-indole-1-carboxylic acid tert-butyl ester, 10 mL dichloromethane, and 0.2 g (0.94 mmol) of sodium triacetoxyborohydride. The reaction was quenched with aqueous sodium bicarbonate. The residue from the organic layer was purified using flash chromatography (ethyl acetate in hexane), yield 130 mg of the free base as colorless oil. LC-MSD, m/z for C23H32N2O2S [M+H]+: 401.6, [M+H-isobutylene]+: 345.5.

後処理

  1. customThe reaction was quenched with aqueous sodium bicarbonate
  2. customThe residue from the organic layer was purified

出典と根拠

ORDレコード
ord-048050004b2a4e109c9173c474fd552d
出典データセット
uspto-grants-2008_08
特許番号
US07417062B2

反応ノート

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