Methyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate → {(3S)-1-[(1R)-1-Phenylethyl]pyrrolidin-3-yl}methanol

HRID 1468760Notes

Reaction equation

HRID 1468760 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O=[C:8]1[N:12]([C@@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[CH2:11][C@@H:10]([C:21](OC)=[O:22])[CH2:9]1>COC1CCCC1>[C:15]1([C@H:13]([N:12]2[CH2:8][CH2:9][C@H:10]([CH2:21][OH:22])[CH2:11]2)[CH3:14])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 13772852Methyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 13772859{(3S)-1-[(1R)-1-Phenylethyl]pyrrolidin-3-yl}methanolYield 57%

Reagents, catalysts & solvents 1

HCID 138539Cyclopentyl methyl etherSolvent

Procedure

To a slurry of lithium aluminum hydride (4.55 g, 120 mmol) in cyclopentyl methyl ether (100 ml) at 0° C. under nitrogen atmosphere was added methyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate (14.0 g, 56.5 mmol) dropwise. The resulting mixture was stirred for 15 minutes and gradually warmed to room temperature. After one hour, the reaction was quenched by the addition saturated sodium sulfate aqueous solution at 0° C. and the resulting solid materials were removed by filtration. Concentration of the filtrate afforded {(3S)-1-[(1R)-1-phenylethyl]pyrrolidin-3-yl}methanol (6.62 g, 32 mmol, 57%). This compound was used for the next reaction without further purification.

Workup

  1. waitAfter one hour
  2. customthe reaction was quenched by the addition saturated sodium sulfate aqueous solution at 0° C.
  3. customthe resulting solid materials were removed by filtration

Sources & evidence

ORD record
ord-d2c9d289db4b41f8a3d6af93a58ee3f2
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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