Trimethylamine → HCID 86641208, compound

Participants

Reaction Steps

To a suspension of (R)-benzyl 3-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)-butanoate (149 mg, 0.38 mmol) in EtOH (2 mL) at 0° C. was added xs Me3N in EtOH (4.2 M, 2 mL, 8.4 mmol). The reaction was sealed and stirred at the temperature for 15 min and then at rt for 3 d. Later, the reaction was concentrated to dryness and purified by preparative TLC (silica gel, 5% MeOH/DCM) to afford the title compound as a colorless gum (43 mg, 37%). 1H NMR (300 MHz, CDCl3): δ=7.35-7.20 (m, 5H), 5.14-5.00 (AB quartet, J=12 Hz, 2H), 4.46 (br, 1H), 3.50-3.25 (m, 2H), 3.24 (s, 9H), 2.85-2.65 (m 2H), 2.70 (s, 3H), 1.38 (s, 9H); MS ESI [M]+, calcd for [C19H31N2O4]+ 351.5 found 351.2 m/z (100).

Provenance & Evidence