Oxiranemethanol, 4-methylbenzenesulfonate, (S)- → Toluene-4-sulfonic acid (s)-2-hydroxy-4-phenylbutyl ester

Temperature

-35 °C

Add phenyl methyl magnesium bromide (14 mL, 14 mmol, 1 M in tetrahydrofuran) to a solution of lithium tetrachlorocuprate (5.5 mL, 0.55 mmol, 0.1 M in tetrahydrofuran) in dry tetrahydrofuran (10 mL) and stir at −35° C. (acetonitrile/dry ice bath) for 15 minutes (J. Med. Chem., 41, 2451-2460, (1998); JOC, 54, 1295-1304, (1989)). Cool to −35° C. a solution of (2S)-(+)-glycidyl tosylate (2.51 g, 11.0 mmol) in dry tetrahydrofuran (4 mL) and transfer rapidly via cannula to the Grignard solution. Stir for 1 hour at −35° C., quench with a saturated aqueous ammonium chloride solution and dilute with diethyl ether. Wash the organic layer with saturated aqueous sodium chloride, dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting with 35:65 ethyl acetate:hexanes) to give the desired compound as a colorless oil (1.77 g, 50%)

1. customquench with a saturated aqueous ammonium chloride solution
2. additiondilute with diethyl ether
3. washWash the organic layer with saturated aqueous sodium chloride
4. dry with materialdry (sodium sulfate)
5. concentrationconcentrate
6. custompurify
7. wash(silica gel chromatography, eluting with 35:65 ethyl acetate:hexanes)

ORD record

ord-0fe8c878f3af4269b56cb8110fc22ece

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07745438B2