Water → HCID 58658603, compound

Participants

Reaction Steps

A suspension of (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-3-carboxylate (2.28 ml; 5.7 mmol) and lithium aluminium hydride (0.216 g; 22.8 mmol) in a mixture of THF (10 ml) and ether (60 ml) was stirred at reflux under argon atmosphere overnight. After addition of water (60 ml), the mixture was stirred for 2 hours. The resulting solid was filtered and the filtrate was evaporated and purified by flash chromatography eluting with a 5–10% gradient of methanol/dichloromethane to give, after evaporation, N-[(5S)-3-hydroxymethyl-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide (yield: 33%) and [(5S)-5-(ethylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl]methanol (yield: 47%).

Provenance & Evidence