1,2-Dichloroethane → HCID 68493244, compound

Participants

Reaction Steps

A mixture of (3S,4S)- and (3R,4R)-methyl 4-aminotetrahydro-2H-pyran-3-carboxylate, HBr (prepared in a similar manner as described in International Patent application No. WO 2003/024899, 500 mg, 2.083 mmol), benzoic acid (254 mg, 2.083 mmol), HOBt (383 mg, 2.499 mmol), EDC (479 mg, 2.499 mmol) and triethylamine (0.581 mL, 4.17 mmol) were mixed in methylene chloride (10 mL) at 25° C. and stirred for 20 hours. At the conclusion of this period, the reaction was worked up by adding methylene chloride and then rinsing the mixture with saturated sodium carbonate (1×). The methylene chloride layer was dried over sodium sulfate and concentrated to give an off-white solid. The off-white solid was purified over silica gel in 3:1 to 1:1 hexanes/EtOAc to 100% EtOAc to yield a mixture of (3R,4R)-methyl 4-benzamidotetrahydro-2H-pyran-3-carboxylate and (3S,4S)-methyl 4-benzamidotetrahydro-2H-pyran-3-carboxylate (500 mg, 1.899 mmol, 91% yield) as a white solid. MS (ESI+)=264.24 (M+H)+.

Provenance & Evidence