(S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide → tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate

HRID 78738

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([O:11][C:12]([NH:14][C@H:15]([C:20](N(C)OC)=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13])([CH3:10])[CH3:9]>CCOCC>[CH:20]([C@@H:15]([NH:14][C:12](=[O:13])[O:11][C:8]([CH3:7])([CH3:10])[CH3:9])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of LiAlH4 (0.356 g, 9.38 mmol) in Et2O (20 mL) at 0° C. was added dropwise a solution of N2-{[(1,1-dimethylethyl)oxy]carbonyl}-N1-methyl-N1-(methyloxy)-L-leucinamide (2.34 g, 8.53 mmol) in Et2O (15 mL). The reaction mixture was stirred for 30 min at 0° C. and quenched with EtOAc (6 mL) followed by 5% aq. potassium bisulfate (6 mL). The reaction mixture was washed with 1 M aq. HCl (2×10 mL), saturated aq. NaHCO3 (2×10 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.

Workup

customquenched with EtOAc (6 mL)
washThe reaction mixture was washed with 1 M aq. HCl (2×10 mL), saturated aq. NaHCO3 (2×10 mL), and brine (10 mL)
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-49fd62e9f4714c8d841a596f58bd85e6
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841463B2

Linked notes

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