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

HRID 2220714Notes

Reaction equation

HRID 2220714 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-048050004b2a4e109c9173c474fd552d
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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