Aluminium lithium hydride → (R)-1-[(3R,4S)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-ethanol

HRID 1944237Notes

Reaction equation

HRID 1944237 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C@@H:10]([C:20](=[O:22])[CH3:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[C@@H:10]([C@H:20]([OH:22])[CH3:21])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 669996811-[(3R,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-ethanone

Product 1

HCID 66999400(R)-1-[(3R,4S)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-ethanolYield 46.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[(3R,4S)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-ethanone (0.52 g, 1.65 mmol) in THF (20 mL) at 0° C. were added portion wise LiAlH4 (55 mg, 1.45 mmol). Stirring was continued for one hour, and the reaction mixture was carefully 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. The two diastereoisomers were separated by column chromatography (SiO2, EtOAc/H, 1:1) to yield (R)-1-[(3R,4S)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-ethanol (V-B-1) 0.24 g (46%) as a white solid ES-MS m/e: 316.1 (M+H+) and (S)-1-[(3R,4S)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-ethanol (V-A-1) 0.25 g (47%) as a white solid ES-MS m/e: 316.1 (M+H+).

Workup

  1. customthe reaction mixture was carefully 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
  6. customThe two diastereoisomers were separated by column chromatography (SiO2, EtOAc/H, 1:1)

Sources & evidence

ORD record
ord-870d2be2e1704f909ef691c1f24bf8ad
Source dataset
uspto-grants-2013_03
Patent number
US08394834B2

Reaction notes

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