HCID 86653293, compound → HCID 67151607, compound

To a stirred, cooled solution of [(5)-3-(4-bromo-phenyl)-1-formyl-propyl]-carbamic acid tert-butyl ester (7.3 g) in THF (40 ml) and Et2O (30 ml) at 0° C. was added dropwise over 30 min a solution of methylmagnesium bromide (20.0 ml, 3 M solution in Et2O). The reaction mixture was then stirred at room temperature for 4 hours before being quenched by dropwise addition of water (gas formation!). The reaction mixture was then poured into EtOAc, the layers were separated and the organic layer was washed sequentially with diluted aq. HCl (pH 5) and saturated brine, then dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, gradient: 0% to 80% EtOAc in hexane) to afford {(1S,2RS)-1-[2-(4-bromo-phenyl)-ethyl]-2-hydroxy-propyl}-carbamic acid tert-butyl ester as a colourless amorphous solid comprising a mixture of epimers (5.1 g, 66%). MS (EI): 303 ([{81Br}M−C4H8]+), 301 ([{79Br}M−C4H8]+), 258 ([{81Br}M−C4H8—CO2H]+), 256 ([{79Br}M−C4H8—CO2H]+), 214, 212, 171, 169, 57 ([C4H9]+).

1. custombefore being quenched by dropwise addition of water (gas formation!)
2. additionThe reaction mixture was then poured into EtOAc
3. customthe layers were separated
4. washthe organic layer was washed sequentially with diluted aq. HCl (pH 5) and saturated brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash chromatography (silica gel, gradient: 0% to 80% EtOAc in hexane)

ORD record

ord-5e9a610ccb7e4ec9a7a556b0f07e4417

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673950B2