Morpholine → HCID 69695131, compound

Participants

Reaction Steps

(1R)-3-Oxo-cyclohexanecarboxylic acid was prepared according to the procedure described by R. D. Allan et al. in Aust. J. Chem., 1981, 34, 2231. A solution of (1R)-3-oxo-cyclohexanecarboxylic acid (1 eq, 2.52 g, 18.1 mmol), 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT, H. Li et al. Organic Letters, 1999, 1, 91) (1.05 eq, 19.0 mmol, 5.68 g) and N,N-diisopropylethylamine (15 eq, 27.1 mmol, 4.7 mL) in anhydrous dichloromethane (70 mL) was allowed to stir at room temperature for 75 minutes. Morpholine (1.2 eq, 21.72 mmol, 1.9 mL) was added and the solution was stirred at ambient temperature for 16 h. The mixture was concentrated under vacuum to an oil which was purified by flash chromatography eluting with a 2.5% methanol-dichloromethane gradient on silica gel to give (3R)-3-(morpholine-4-carbonyl)-cyclohexanone (2.05 g, 54%).

Provenance & Evidence