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

Participants

Reaction Steps

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

Provenance & Evidence