Acetic Acid → (+/-)-2-Methyl-3-((2-nitro)benzylamino)-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide

Participants

Reaction Steps

A mixture of (±)-2-Methyl-3-amino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide (94 mg), 3-nitrobenzaldehyde (40 mg), glacial acetic acid (90 μl), and sodium triacetoxyborohydride (78 mg) in dichloromethane (5 ml) was stirred overnight. The reaction mixture was partitioned between aq. K2CO3 (1N, 10 mL) and ethyl acetate (5 ml). The aqueous was washed with EtOAc (5 mL×2). Organic layers were combined, washed with brine, dried with anhydrous sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica (20-50% ethyl acetate in hexane) and yielded (±)-2-Methyl-3-((2-nitro)benzylamino)-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide as a resin: MS (m+1)=490.3.

Provenance & Evidence