(S,E)-N-(2-(tert-butyldimethylsilyloxy)ethylidene)-2-methylpropane-2-sulfinamide synthesis
- Product Name:(S,E)-N-(2-(tert-butyldimethylsilyloxy)ethylidene)-2-methylpropane-2-sulfinamide
- CAS Number:918413-70-4
- Molecular formula:C12H27NO2SSi
- Molecular Weight:277.5
102191-92-4
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Yield:918413-70-4 94%
Reaction Conditions:
with copper sulfate in dichloromethane at 20; for 48 h;
Steps:
84.1
A mixture of 2-(tert-butyldimethylsilyloxy)acetaldehyde (54.64 mL,258.2 mmol) in DCM (500 mL) was treated with (S)-2-methylpropane-2-sulfinamide (34.42 g, 284.0 mmol), followed by copper sulfate (103.0 g, 645.4 mmol) at ambient temperature. After stirring for 48 hours, the mixture was filtered through Celite and washed with DCM. The mixture was concentrated and purified on silica gel (10-30% EtOAc in hexane) to provide (S,E)-N-(2-(tert-butyldimethylsilyloxy)ethylidene)-2-methylpropane-2-sulfinamide (67.3 g, 94% yield).
References:
ARRAY BIOPHARMA INC.;ANDREWS, Steven W.;CONDROSKI, Kevin Ronald;DE MEESE, Lisa A.;FELL, Jay Bradford;FISCHER, John P.;LE HUEROU, Yvan;JOSEY, John A.;KOCH, Kevin;MIKNIS, Gregory F.;RODRIGUEZ, Martha E.;TOPALOV, George T.;WALLACE, Eli M.;XU, Rui WO2011/29027, 2011, A1 Location in patent:Page/Page column 121
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