Tetrahydrofuran → HCID 178472362, compound

Participants

Reaction Conditions

Reaction Steps

trans-Ethyl 4-(5-bromothiazole-2-carbonyl)cyclohexanecarboxylate (150 mg, 0.433 mmol), sodium cyanoborohydride (63 mg, 1.00 mmol), ammonium acetate (83 mg, 1.08 mmol), THF (0.6 mL), and methanol (1.8 mL) were combined in a sealed vial and heated to a temperature of 80° C. for 16 hours. The mixture was cooled to 23° C. and subsequently transferred to a separatory funnel containing EtOAc. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered and concentrated to afford crude trans-ethyl 4-(amino(5-bromothiazol-2-yl)methyl)cyclohexanecarboxylate, which was used directly in the subsequent synthetic transformation without purification. MS ESI calc'd. For C13H20BrN2O2S [M+H]+ 347, 349. found 347, 349.

Provenance & Evidence