Aluminium lithium hydride → 3-Pyrrolidinemethanol, 4-(4-chlorophenyl)-3-methyl-1-(phenylmethyl)-

HRID 1891321Notes

Reaction equation

HRID 1891321 reaction equation
C([O:3][C:4]([C:6]1([CH3:25])[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:9][N:8]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:18]([N:8]1[CH2:9][CH:10]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[C:6]([CH2:4][OH:3])([CH3:25])[CH2:7]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66653488HCID 66653488, compound

Product 1

HCID 666532933-Pyrrolidinemethanol, 4-(4-chlorophenyl)-3-methyl-1-(phenylmethyl)-Yield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (3RS,4RS)-1-benzyl-4-(4-chloro-phenyl)-3-methyl-pyrrolidine-3-carboxylic acid ethyl ester (5.75 g, 16.7 mmol) in THF (200 mL) at 0° C., was added portion wise LiAlH4 (381 mg, 10.0 mmol) over 20 minutes. After one hour at this temperature, the reaction mixture was carefully quenched by addition of icy water and then of an aqueous solution of NaHCO3. The product was extracted with EtOAc several times, the combined organic phases were dried over NA2SO4 and purification by column chromatography (SiO2, EtOAc/H 1:4 to 1:1) yielded the title product (4.0 g, 76%) as a colorless viscous oil. ES-MS m/e: 316.2 (M+H+).

Workup

  1. customthe reaction mixture was carefully quenched by addition of icy water
  2. extractionThe product was extracted with EtOAc several times
  3. dry with materialthe combined organic phases were dried over NA2SO4 and purification by column chromatography (SiO2, EtOAc/H 1:4 to 1:1)

Sources & evidence

ORD record
ord-33bc395525f94673a4c5ad776ea16a7b
Source dataset
uspto-grants-2013_08
Patent number
US08507535B2

Reaction notes

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