(R,S)-1-Tosyl Glycerol-d5 synthesis

Yield:928623-32-9 90%

Reaction Conditions:

Stage #1: allyl-d5 4-methylbenzenesulfonatewith AD-mix-β;water;tert-butyl alcohol at 0; for 18 h;
Stage #2: with sodium hydrogensulfite in water;tert-butyl alcohol at 0 - 20; for 1 h;

Steps:

v

AD-Mix-β (8.17g) was added to a mixture of tert-butyl alcohol (27.5 mL) and water (27.5 mL) cooled to 0 ⁰C. After a short time, allyl 4- methylbenzenesulonate-d₅ (1.28 g, 5.9 mmol) was added drop- wise to the orange suspension and the mixture was stirred at 0 ⁰C for 18 hours. NaHSO₃ (8.8 g, 46.2 mmol) was added in portions and the reaction mixture was allowed to warm to room temperature and stirred for a further hour. The reaction mixture was extracted with ethyl acetate (5 x 30 mL) and the organic extracts were combined and passed through a short pad of silica before being concentrated in vacuo. Recrystallisation yielded the desired product as a hydroscopic white solid (1.32 g, 90%). The ¹U NMR, ¹³C NMR, IR and MS spectra are consistent with the indicated structure

References:

WO2007/26140,2007,A2 Location in patent:Page/Page column 23; 25