Diethanolamine → HCID 12072785, compound

Participants

Reaction Conditions

Reaction Steps

To 8-cyclohexylmethoxy-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-7carboxylic acid amide (4.0 g, 13.3 mmol) suspended in CH2Cl2 (25 mL) at 42° C. was added (+)-DIP-Chloride (25 mL of CH2Cl2). The mixture was stirred at −12° C. for 18 h, concentrated, diluted with Et2O (200 mL) and treated with diethanolamine (5.1 mL, 53.1 mmol). After stirring for 2.5 h, the formed solids were filtered and washed with Et2O. The filtrate was concentrated, and the residue purified by silica gel column chomatography (5% MeOH/CH2Cl2) to a white solid (3.2 g, 80%). m.p. 164-165° C. Optical purity determined by Mosher Amide formation, 71% e.e.

Provenance & Evidence