Methanol → HCID 86640052, compound

Participants

Reaction Steps

Mix (±)-N-[7-cyano-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl]-isobutyramide (5 g, 18.7 mmol) and Al—Ni catalyst (15 g) in water/96% formic acid, 1/10 (110 mL). Reflux for 18 h, add Al—Ni catalyst (13 g) and reflux another 5 h. Cool and dilute with MeOH and filter off the inorganics. Concentrate the filtrate, add EtOH (200 mL) and sonicate for 15 min. Filter insoluble material and to the crude aldehyde solution add O-methoxyamine-HCl (120 mmol) dissolved in water (25 mL) and make the mixture basic (pH=9-12) with 5.0 N NaOH. Stir at room temperature for 18 h and remove most of the solvent under reduced pressure. Mix the residue with water and sonicate for 30 min. Isolate 4.39 g of a brown solid. Purify the material on silica gel using 30-100% EtOAc/hexane to give 530 mg (10%) title compound as a pale yellow solid. MS (m/z): 300 (M+1), 298 (M−1).

Provenance & Evidence