4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoic acid → Tert-butyl 2-(cyclopropylmethoxy)-4-(hydroxymethyl)phenyl(methylsulfonyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoic acid (for reference procedure see Example 18, WO 2010/089107, which is incorporated herein by reference in its entirety) (0.500 g, 1.297 mmol) in anhydrous THF (10 ml), BH3*THF complex (1M solution in THF, 2.59 ml, 2.59 mmol) was added drop wise at RT under nitrogen atmosphere. After 4 hours, the reaction was cooled to 0° C. and quenched with aqueous NH4Cl. The mixture was extracted with EtOAc and the organic phase was dried over Na2SO4 and evaporated under reduced pressure affording tert-butyl 2-(cyclopropylmethoxy)-4-(hydroxymethyl)phenyl(methylsulfonyl)carbamate as a colorless oil (0.430 g, 1.158 mmol, 89% yield, MS/ESI+ 394.2 [MNa]+). This product was used without purification.

Provenance & Evidence