Aluminium lithium hydride → tert-Butyl(1-(4-bromophenyl)-3-((2-(hydroxymethyl)benzyl)oxy)propan-2-yl)carbamate

HRID 1429363Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:10][O:11][CH2:12][C:13]2[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=2[C:15](OC)=[O:16])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[C:27]([O:26][C:24](=[O:25])[NH:23][CH:9]([CH2:10][O:11][CH2:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[CH2:15][OH:16])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of compound 3g (5 g, 10 mmol) in dry ether (80 mL) was added slowly LiAlH4 (1M in THF, 15.7 mL, 15.7 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min. Then the mixture was quenched with water (1 mL) under vigorous stirring. The precipitate was removed by filtration and the filtrate was concentrated in vacuo to give 3h as a white solid (4.3 g, 92% yield).

Workup

customThen the mixture was quenched with water (1 mL) under vigorous stirring
customThe precipitate was removed by filtration
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-388502bbe1194de1ace1243f2daa2972
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940722B2

Reaction notes

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