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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1061653Generated: November 2, 2026

Ethanol → (2RS,3S)-3-(Benzyloxycarbonyl)amino-4-phenyl-1,2-butanediol

https://huagongshe.com/reaction/1061653

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantLithium BromideHCID 82050—
ReactantSodium borohydrideHCID 4311764—
ReactantIsopropyl (2RS,3S)-3-(benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyrateHCID 60073836—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
Product(2RS,3S)-3-(Benzyloxycarbonyl)amino-4-phenyl-1,2-butanediolHCID 60073850—

Reaction Steps

Ethanol (1 ml) and lithium bromide (36.7 mg) are added to a solution of isopropyl (2RS,3S)-3-(benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyrate (150 mg, Reference compound No. 13-1) in tetrahydrofuran (1 ml). The mixture is cooled with ice, sodium borohydride (42.1 mg) is added to the mixture, and the temperature is raised to room temperature. The whole is stirred overnight, water is added thereto, and the whole is further stirred for one hour. The reaction mixture is concentrated under reduced pressure, and the resulting residue is extracted with ethyl acetate. The extract is washed with saturated brine and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure to give the titled reference compound (105 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06960575B2
Source datasetuspto-grants-2005_11
ORD IDord-8aad0e06e2514dcc847015f7deb1eda7
Source noteuspto-grants-2005_11