Methanol → 1429182-35-3

To a solution of (S)-tert-butyl 2-methyl-4-oxopentan-3-ylcarbamate (2.65 g, 12.31 mmol) in MeOH (30 mL) at 0° C. was added portion wise NaBH4 (0.931 g, 24.62 mmol). Cold bath was removed and the reaction was stirred for 1 hour. HCl solution (1 M, 0.3 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. The residue was purified via silica gel flash chromatography (10-50% EtOAc-Hexanes) to afford the desired product as a white solid (2.05 g). LCMS m/z 240.2 (M+Na)+, Rt 0.69 min.

1. customCold bath was removed
2. additionHCl solution (1 M, 0.3 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
11. customThe residue was purified via silica gel flash chromatography (10-50% EtOAc-Hexanes)

ORD record

ord-9815f2bd446b4e39b7b22b1ac7d937fa

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957068B2