Sodium Bicarbonate → HCID 67302850, compound

Participants

Reaction Steps

Under an argon atmosphere, a solution of benzyl 2-(adamantan-2-ylidene)hydrazinecarboxylate (1.60 g, 5.40 mmol) in tetrahydrofuran (54 mL) was added with sodium cyanoborohydride (370 mg, 5.90 mmol) at room temperature, to which a solution of p-toluenesulfonic acid monohydrate (190 mg, 1.00 mmol) in tetrahydrofuran (10 mL) was dropped. The resultant was stirred at the same temperature for 5 hours. The reaction solution was added with a saturated aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, and benzyl 2-(adamantan-2-yl)hydrazinecarboxylate (1.54 g, 94.9%) was obtained as a white crystalline powder.

Provenance & Evidence