Aluminium lithium hydride → tert-butyl N-[2-(3,5-difluorophenyl)-1-oxopropan-2-yl]carbamate

HRID 1866683Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]([C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=1)([CH3:17])[C:10](OC(C)(C)C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:24][C:22]1[CH:23]=[C:18]([C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:17])[CH:10]=[O:11])[CH:19]=[C:20]([F:25])[CH:21]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of tert-butyl 2-[(tert-butoxycarbonyl)amino]-2-(3,5-difluorophenyl)propanoate from Step B (2.00 g, 5.60 mmol) in THF (20 mL) at −78° C. was added LiAlH4 (5.60 mL of a 1 M solution in THF, 5.60 mmol), dropwise. The reaction mixture was stirred at −78° C. for 6 h, then quenched with EtOAc (5.6 mL), then H2O (15.6 mL), then 1 N aqueous NaOH (5.6 mL), then EtOAc (17 mL). The reaction mixture was warmed to ambient temperature, stirred for 1 h, filtered, and extracted with EtOAc (2×40 mL). The organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound in sufficient purity for use in the next step. MS: m/z=186 (M−CO2C4H7).

Workup

customquenched with EtOAc (5.6 mL)
temperatureThe reaction mixture was warmed to ambient temperature
stirringstirred for 1 h
filtrationfiltered
extractionextracted with EtOAc (2×40 mL)
dry with materialThe organic extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0525dc4d25f5458cb089c674373fa76b
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629338B2

Reaction notes

Loading…