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

HRID 1061653Notes

Reaction equation

HRID 1061653 reaction equation
C(O)C.[Br-].[Li+].[CH2:6]([O:13][C:14]([NH:16][C@@H:17]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:18]([OH:25])[C:19](OC(C)C)=[O:20])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[BH4-].[Na+]>O1CCCC1.O>[CH2:6]([O:13][C:14]([NH:16][C@@H:17]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH:18]([OH:25])[CH2:19][OH:20])=[O:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 82050Lithium BromideHCID 4311764Sodium borohydrideHCID 60073836Isopropyl (2RS,3S)-3-(benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyrate

Product 1

HCID 60073850(2RS,3S)-3-(Benzyloxycarbonyl)amino-4-phenyl-1,2-butanediol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. additionis added to the mixture
  2. stirringthe whole is further stirred for one hour
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. extractionthe resulting residue is extracted with ethyl acetate
  5. washThe extract is washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe extract is concentrated under reduced pressure

Sources & evidence

ORD record
ord-8aad0e06e2514dcc847015f7deb1eda7
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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