Aluminium lithium hydride → benzyl 4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate

HRID 1179485Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26](OC)=[O:27])=[CH:20][CH:19]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[OH:27][CH2:26]/[CH:25]=[CH:24]/[C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])[O:14][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:19][CH:20]=1

Participants

Conditions

Temperature: -20 °C

Procedure

A THF solution of LiAlH4 (6.75 mL of a 1.0 M solution, 6.75 mmol) was added to a cooled (−78° C.) solution of methyl (2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)acrylate (2.1 g, 6.75 mmol) in TBF (34 mL). The solution was allowed to warm slowly to −20° C. and maintained at that temperature for 2 hours. The reaction mixture was quenched by slow addition of saturated NH4Cl and then treated with dilute citric acid. The resulting solution was stirred for 15 minutes and then extracted with three portions of ethyl acetate. The combined organic phases were washed with H2O, brine and dried (MgSO4), filtered and concentrated to give an oil. The crude product was purified by column chromatography (20-50% ethyl acetate-hexane) to provide the title compound as a yellow solid.

Workup

temperaturemaintained at that temperature for 2 hours
customThe reaction mixture was quenched by slow addition of saturated NH4Cl
additiontreated with dilute citric acid
extractionextracted with three portions of ethyl acetate
washThe combined organic phases were washed with H2O, brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto give an oil
customThe crude product was purified by column chromatography (20-50% ethyl acetate-hexane)

Sources & evidence

ORD record: ord-b2e918b68efb4f408b03cca71023086a
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279494B2

Reaction notes

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