(-)-2,2,2-Trifluoro-1-(9-anthryl)ethanol → (1r)-1-Methylthiocarbonyloxyethyl benzoate

Participants

Reaction Steps

1-Methylthiocarbonyloxyethyl benzoate (2g) (50 g), prepared as described in Gallop et al., U.S. Pat. No. 7,227,028, and lipase from Candida rugosa (2.5 g) were stirred in phosphate buffered saline, pH 7.2, (0.5 L) at room temperature. The progress of the reaction was monitored by 1H-NMR using the chiral solvating agent [(R)-(+)-2,2,2-trifluoro-1-(9-anthryl)ethanol] and was complete within 16 h. The reaction mixture was diluted with ether and the ether layer separated and filtered through a pad of CELITE® to remove the enzyme. The ether phase was washed repeatedly with aqueous sodium bicarbonate then brine, and dried over anhydrous sodium sulfate (Na2SO4). Removing the solvent in vacuo afforded 22 g of the title compound (5) as a single enantiomer. 1H NMR (CDCl3, 400 MHz): δ 1.65 (d, J=5.6 Hz, 3H), 2.35 (s, 3H), 7.20 (q, J=5.6 Hz, 1H), 7.45 (m, 2H), 7.58 (m, 1H), 8.06 (m, 2H) ppm.

Provenance & Evidence