(Diethylamino)sulfur trifluoride → HCID 86677912, compound

Participants

Reaction Steps

A solution of ((R)-2-Hydroxy-1,2-dimethyl-propyl)-carbamic acid tert-butyl ester (4 g, 19.68 mmol) in CH2Cl2 (100 mL) at −78° C. was added DAST (2.86 mL, 21.65 mmol) dropwise and the resulting mixture was warmed to rt and stirred for 16 hrs. The reaction mixture was quenched with sat. NaHCO3 (100 mL). The organic phase was saved. The water layer was extracted with CH2Cl2 (100 mL×2). The combined organic phases were washed with 50 mL of water and 50 mL of brine and dried over Na2SO4. Filtration and concentration yielded a crude product which was purified on silica gel column with hexanes/EtOAc (10/1) to yield the title compound (2.65 g, 66%). 1H-NMR (400 MHz, CDCl3) δ ppm 3.65-3.80 (1 H, m), 1.46 (9 H, s), 1.39 (3 H, d, J=2.6 Hz), 1.34 (3 H, d, J=2.2 Hz), 1.19 (3 H, d, J=6.8 Hz). 19F NMR (376 MHz, with 1H coupling, CDCl3) δ ppm −155.78, −155.39 (1 F, m).

Provenance & Evidence