Water → HCID 58972204, compound

Participants

Reaction Steps

To a stirred solution of {(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-methyl-propyl}-carbamic acid tert-butyl ester (8.84 g, 16.8 mMol) in acetonitrile (150 ml) is added H2O (1.52 ml, 84.3 mMol) and Sc(OTf)3 (83 mg, 0.2 mMol). The reaction is stirred at RT for 3 hours. The reaction mixture is then poured onto a biphasic mixture of AcOEt and NaHCO3 (saturated aqueous solution). The aqueous phase is extracted with AcOEt (3 times). The combined organic layers are dried (Na2SO4) and concentrated under reduced pressure. Column chromatography eluting with 0%→40% AcOEt in heptane gives {(R)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-1-hydroxymethyl-1-methyl-propyl}-carbamic acid tert-butyl ester as a colourless oil.

Provenance & Evidence