HCID 71059906, compound → HCID 71059530, compound

Participants

Reaction Steps

Starting from (R)—N-((4R)-6-bromo-4-(1,1-difluoro-2-hydroxyethyl)-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-yl)-2-methylpropane-2-sulfinamide (intermediate B4.7), and after chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to =:100 as the eluent the 2-((2R,4R)-4-amino-6-bromo-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-yl)-2,2-difluoroethanol (47% yield) (intermediate B5.7A) was obtained as the first eluting isomer as a white foam; MS (ISP): m/z=378.0 [M+H]+ and 380.0 [M+2+H]+. The second eluting isomer, 2-((2S,4R)-4-amino-6-bromo-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-yl)-2,2-difluoro ethanol (27% yield) (intermediate B5.7B) was also obtained as a white foam; MS (ISP): m/z=378.0 [M+H]+ and 380.0 [M+2+H]+.

Provenance & Evidence