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

HRID 20364

Reaktionsgleichung

[C:1]1([Mg]C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-].[C:10](#N)C.C(=O)=O.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:26][CH2:27][C@H:28]2[O:30][CH2:29]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1>O1CCCC1>[OH:30][C@@H:28]([CH2:29][CH2:10][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:27][O:26][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

Komponenten

Reaktionsbedingungen

Temperatur: -35 °C

Versuchsvorschrift

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%)

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-0fe8c878f3af4269b56cb8110fc22ece
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07745438B2

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