Dimethylamine → HCID 15871737, compound

Participants

Reaction Steps

Dimethylamine (0.18 g, 4.0 mmol) was added to ethyl trans-7-chloro-5-(1-naphthyl)-1-(2-formyl-2-methylpropyl)-2-oxo-1,2,3,5-tetrahydro-4,1 -benzoxazepine-3-acetate (2.0 g, 4.05 mmol) in titanium tetraisopropoxide (3.45 g, 12.15 mmol) at room temperature. Stirring for 1h was followed by addition of sodium cyanoborohydride (0.38 g, 6.0 mmol) and ethanol (20 ml). The mixture was stirred for another 18 hours before 2 N sodium hydroxide was added. The mixture was extracted several times with dichloromethane, and the combined organic layers were dried with MgSO4. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography (dichloromethane/ methanol/aqueous ammonia 99:1:0.1 to 98:2:0.2) to give the title compound (1.23 g, 58%) as a yellow oil.

Provenance & Evidence