Dimethylamine → HCID 69660796, compound

Participants

Reaction Steps

A solution of (3S)-3-(5-fluoro-1H-indol-3-yl)-cyclopentanone (290 mg, 1.34 mMol), dimethylamine (2.0 M solution in THF, 6.7 mL, 13.4 mMol) in ethanol (10 mL) was stirred for 15 min. Sodium triacetoxyborohydride (1.1 g, 5.4 mMol) was added and the reaction stirred for 1 h. The reaction was extracted three times with ethyl acetate/aqueous sodium bicarbonate solution. The ethyl acetate extracts were dried over magnesium sulfate and concentrated in vacuo to give (3S)-3-(5-fluoro-1H-indol-3-yl)-cyclopentyl-dimethylamine (400 mg, 100%) as a cis/trans diastereomeric mixture. The diastereomeric mixture was separated by preparative chiral HPLC using a Chiralpak AD column (50×500 mm with 20 μm packing) and 10% ethanol/hexane (0.1% diethylamine added in hexane as modifier) as the eluent at a flow rate of 60 mL/min for 50 min. The UV detector was set at 280 nm, the injection loop volume was 10 mL, and the injection load was 35–165 mg in a ethanol/hexane (1:1) solution.

Provenance & Evidence