1-Benzothiophene-2-carbaldehyde → (S)-2-{[(Benzo[b]thiophen-2-ylmethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 2220712Notes

Reaction equation

HRID 2220712 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[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24][NH2:25])=[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[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24][NH:25][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 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58622178(S)-2-{[(Benzo[b]thiophen-2-ylmethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl esterYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Experimental conditions were analogous to Example 1, from 0.28 g (1.78 mmol) of benzo[b]thiophene-2-carbaldehyde, 0.35 g (1.78 mmol) of (S)-2-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester, 10 mL dichloromethane, and 565 mg (2.64 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). The reaction gave 291 mg of the free base as a colorless oil. LC-MSD, m/z for C19H26N2O2S [M+H]+: 347.5

Workup

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

Sources & evidence

ORD record
ord-fadda18a09c045c3a675d43786db29d4
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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