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

HRID 2220714노트

반응식

HRID 2220714 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-048050004b2a4e109c9173c474fd552d
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417062B2

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