t-Butyl 3-(4-bromophenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate → t-Butyl 1-(4-bromophenyl)-3-oxohexan-2-ylcarbamate

A solution of propylmagnesium bromide (29.7 g, 201.6 mmol, 3.0 equiv) in THF (200 mL) was added dropwise with stirring at 0° C. to a solution of the carbamate (26 g, 66.5 mmol, 1.0 equiv) in THF (200 mL). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of aqueous NH4Cl (200 mL). The resulting solution was extracted with EtOAc and the organic layers combined. The resulting mixture was washed with saturated NaHCO3 (200 mL) and saturated aqueous NaCl (200 mL), then dried over anhydrous MgSO4. The residue was applied onto a silica gel column with petroleum ether/EtOAc (5:1) to yield t-butyl 1-(4-bromophenyl)-3-oxohexan-2-ylcarbamate (14 g) as a white solid.

1. customThe reaction was then quenched by the addition of aqueous NH4Cl (200 mL)
2. extractionThe resulting solution was extracted with EtOAc
3. washThe resulting mixture was washed with saturated NaHCO3 (200 mL) and saturated aqueous NaCl (200 mL)
4. dry with materialdried over anhydrous MgSO4

ORD record

ord-94c4131c90f641b39da909f35edc7472

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598170B2