(S)-2-(Boc-Amino)-N-methoxy-n-methylbutyramide → tert-butyl N-((2S)-1-oxobutan-2-yl)carbamate

Temperature

0 °C

To a solution of LiAlH4 (0.453 g, 11.9 mmol) in Et2O (20 mL) at 0° C. was added dropwise a solution of 1,1-dimethylethyl ((1S)-1-{[methyl(methyloxy)amino]carbonyl}-propyl)carbamate (2.67 g, 10.8 mmol) in Et2O (15 mL). The reaction mixture was stirred for 30 min at 0° C. and quenched with EtOAc (6.5 mL) followed by 5% aq. potassium bisulfate (6.5 mL). The reaction mixture was washed with 1 M aq. HCl (3×10 mL), saturated aq. NaHCO3 (3×10 mL), and brine (10 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound as a clear, colorless oil.

1. customquenched with EtOAc (6.5 mL)
2. washThe reaction mixture was washed with 1 M aq. HCl (3×10 mL), saturated aq. NaHCO3 (3×10 mL), and brine (10 mL)
3. dry with materialThe organic layer was dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo

ORD record

ord-5760667bccfa440ab1833c283b8e4596

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841463B2