Reacción #48642

Ecuación de reacción

phenyl methyl magnesium bromide

(2S)-(+)-glycidyl tosylate

acetonitrile dry ice

→

desired compound

Rendimiento 50.0%

Toluene-4-sulfonic acid (S)-2-hydroxy-4-phenylbutyl ester

Rendimiento 50.0%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquench with a saturated aqueous ammonium chloride solution
2. 2
   workup.ADDITIONdilute with diethyl ether
3. 3
   LavadoWash the organic layer with saturated aqueous sodium chloride
4. 4
   Secadodry (sodium sulfate)
5. 5
   Concentraciónconcentrate
6. 6
   Otropurify
7. 7
   Lavado(silica gel chromatography, eluting with 35:65 ethyl acetate:hexanes)

Procedimiento

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%)

Fuente