Potassium Hydroxide → tert-butyl (S)-1-(carbamoylmethylamino)-3-cyclohexyl-propan-2-ylcarbamate

Participants

Reaction Steps

To a solution of 2-aminoacetamide hydrochloride (0.13 g, 1.13 mmol) in MeOH (1 mL) was added KOH (18 mg). When the solid had completely dissolved, the tert-butyl (S)-2-cyclohexyl-1-formylethylcarbamate from Step 1 was added in one portion, and the resulting suspension was stirred for 15 minutes. A solution of sodium cyanoborohydride (0.18 g, 2.7 mmol) in MeOH (1 mL) was added dropwise. The resulting solution was stirred at rt until no aldehyde remained (˜40 min). The solvent was removed under vacuum and the residue was distributed between ether and water (10 mL/10 mL). The water layer was extracted with ether (2×5 mL). The combined ether layers were dried, and solvent was removed under vacuum to give tert-butyl (S)-1-(carbamoylmethylamino)-3-cyclohexyl-propan-2-ylcarbamate as an oil, which was used for the next step without purification. MS ESI +ve m/z 314 (M+1).

Provenance & Evidence