Ethyl Acetate → tert-Butyl [4-(hydroxymethyl)benzyl]carbamate

HRID 1067794Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([NH:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([O-])=[O:21])=[CH:18][CH:17]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C(OCC)(=O)C>O1CCCC1>[C:7]([O:11][C:12]([NH:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][OH:21])=[CH:23][CH:24]=1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 1.40 g (36.8 mmol) of lithium aluminum hydride in 150 ml of tetrahydrofuran was stirred at 0° C. A solution of 13.0 g (49.0 mmol) of 4-(tert-butoxycarbonylaminomethyl)benzoate in 50 ml of tetrahydrofuran was dropwise added slowly to the suspension. After completion of the dropwise addition, the solution was heated to reflux for 2 hours and then cooled to 0° C. After 20 ml of 50% tetrahydrofuran was dropwise added to the reaction mixture, 100 ml of ethyl acetate was added thereto. Insoluble matters were filtered off and the resulting filtrate was concentrated under reduced pressure. The concentrate was isolated and purified by silica gel column chromatography to obtain 8.80 g (75.7%) of 4-(tert-butoxycarbonylaminomethyl)benzyl alcohol.

Workup

additionAfter completion of the dropwise addition
temperaturethe solution was heated
temperatureto reflux for 2 hours
temperaturecooled to 0° C
additionwas added
filtrationInsoluble matters were filtered off
concentrationthe resulting filtrate was concentrated under reduced pressure
customThe concentrate was isolated
custompurified by silica gel column chromatography

Sources & evidence

ORD record: ord-6130da90db0244ab90175c2d780325f5
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248772B1

Reaction notes

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