Dimethylformamide → HCID 71305905, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 165d (400 mg, 1.57 mmol) and N,N-dimethylformamide (0.1 mL) in DCM (5 mL) was added oxalyl chloride (397 mg, 3.13 mmol) dropwise. See FIG. 6. The reaction mixture was stirred at 15° C. for 2.5 h and then concentrated. The residue was dissolved in tetrahydrofuran (20 mL) and added dropwise to aqueous ammonia (10 mL, 28%). The mixture was stirred at 15° C. for 4 h and then diluted with water (15 mL). The reaction mixture was extracted with EtOAc (15 mL×3). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to afford tert-butyl 1-carbamoyl-6-azaspiro[2.5]octane-6-carboxylate 165e (260 mg, 65%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 5.58 (s, 1H), 5.34 (s, 1H), 3.48-3.39 (m, 4H), 1.73-1.70 (m, 2H), 1.48 (s, 9H), 1.47-1.41 (m, 2H), 1.40-1.22 (m, 2H), 0.89-0.87 (m, 1H).

Provenance & Evidence