Hydrochloric Acid → HCID 67266052, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 3-oxo-2,2-diphenylpropylcarbamate (0.10 g, 0.307 mmol) in DMF (4 mL) and trimethylorthoformate (4 mL) was treated with neopentylamine (0.054 g, 0.615 mmol), sodium triacetoxyborohydride (0.098 g, 0.461 mmol) and acetic acid (2 drops) and the reaction was stirred at 23° C. overnight. LC/MS shows only formation of the imine. The reaction was then treated with sodium borohydride (0.050 g, 1.32 mmol) and methanol (˜2 mL) and stirred at 23° C. for 30 minutes. The reaction was acidified with 1N HCl and washed with diethyl ether. The aqueous phase was basified with sat. aq. sodium bicarbonate, extracted with diethyl ether (3×) and the combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude tert-butyl 3-(neopentylamino)-2,2-diphenylpropylcarbamate (0.055 g, 45%) as an oil. 1H NMR (400 MHz, CDCl3) δ: 0.82 (9H, s), 0.92-0.96 (2H, m), 1.42 (9H, s), 2.35 (2H, s), 3.47 (2H, s), 3.86 (2H, d, J=4.80 Hz), 7.15 (1H, br s), 7.17-7.26 (6H, m), 7.28-7.34 (4H, m). HPLC ret. time (Condition A): 2.68 min. LC/MS (M+H)+: 397.

Provenance & Evidence