Triethylamine → HCID 90238121, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl ((2S)-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxypropan-2-yl)carbamate (2.0 g, 5.16 mmol) and triethylamine (1.15 ml, 8.26 mmol) at 0° C. in DCM (20 ml) was added methanesulfonyl chloride (0.48 ml, 6.2 mmol). The reaction was stirred at 0° C. for 1 hour and then was quenched with a saturated solution of NH4Cl. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated. The product was purified by column chromatography to yield (2S)-1-(3,5-bis(trifluoromethyl)phenyl)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate. The crude material was judged to have a 9:1 diastereomeric ratio by 1H NMR analysis. 1H NMR (500 MHz, CDCl3): δ 7.91 (s, 1H); δ 7.87 (s, 0.1H); δ 7.84 (s, 2H); 5.73 (d, J=4.3 Hz, 1H); δ 5.21 (d, J=7.0 Hz, 0.1H); δ 4.58 (s, 1H); 4.18 (br s, 1H); 3.02 (s, 3H); 1.39 (s, 9H); 1.25 (d, J=6.9 Hz, 3H).

Provenance & Evidence