Aluminium lithium hydride → [(3SR,4RS)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methanol

HRID 906912Notes

Reaction equation

HRID 906912 reaction equation
C([O:3][C:4]([CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH2:9][N:8]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:19]([N:8]1[CH2:9][CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH:6]([CH2:4][OH:3])[CH2:7]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67131665Ethyl 1-benzyl-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate

Product 1

HCID 67131569[(3SR,4RS)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methanolYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3SR,4RS)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (1.00 g, 2.64 mmol) in THF (15 mL) at 0° C. were added portion wise LiAlH4 (211 mg, 5.56 mmol). Stirring was continued for 2 hours, and the reaction mixture was quenched by addition of aq. NH4Cl, concentrated under vacuo and the product extracted with EtOAC. The combined organic phases were dried on Na2SO4 and concentrated under vacuo. Flash chromatography (SiO2, EtOAc) to yield 0.70 g (79%) of the title product as a white solid ES-MS m/e: 336.3 (M+H+).

Workup

  1. customthe reaction mixture was quenched by addition of aq. NH4Cl
  2. concentrationconcentrated under vacuo
  3. extractionthe product extracted with EtOAC
  4. customThe combined organic phases were dried on Na2SO4
  5. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-5449e174a13044cb90491133cf115bae
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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