Sodium borohydride → 1429182-35-3

To a solution of tert-butyl 2-methyl-3-oxobutan-2-ylcarbamate (2.36 g, 11.73 mmol) in MeOH (30 mL) at 0° C. was added portion wise NaBH4 (0.887 g, 23.45 mmol). Cold bath was removed and the reaction was stirred for 1 hour. HCl solution (1 M, 0.2 mL) was then added cautiously to quench the reaction. The reaction mixture was then concentrated and diluted with EtOAc (50 mL) and water (10 mL). The phases were separated and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organics were then dried (Na2SO4) and concentrated under reduced pressure. The residue was purified via silica gel flash chromatography (10-50% EtOAc-Hexanes) to afford the desired product as a white solid (2.12 g). LCMS m/z 204.1 (M+H)+, Rt 0.69 min.

1. customCold bath was removed
2. additionHCl solution (1 M, 0.2 mL) was then added cautiously
3. customto quench
4. customthe reaction
5. concentrationThe reaction mixture was then concentrated
6. additiondiluted with EtOAc (50 mL) and water (10 mL)
7. customThe phases were separated
8. extractionthe aqueous layer was extracted with EtOAc (2×20 mL)
9. dry with materialThe combined organics were then dried (Na2SO4)
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified via silica gel flash chromatography (10-50% EtOAc-Hexanes)

ORD record

ord-97bc390e53234788b002dc154cb3976c

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957068B2