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

HRID 565008Notes

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 imol) 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-7e1e0045802f40348088c1580019fd3c
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06169107A

Reaction notes

Loading…