1,4-Dibromobutane → 1-Phenyl-2-(pyrrolidin-1-yl)propan-1-ol

HRID 341946

Reaction equation

HRID 341946 reaction equation
Cl.[CH3:2][CH:3]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].C[C@H](N)[C@H](O)C1C=CC=CC=1.BrCCCCBr.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:2][CH:3]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]

Participants

6

Reactant 4

HCID 80561,4-DibromobutaneHCID 10297PhenylpropanolamineHCID 516892Sodium BicarbonateHCID 53395958beta-Methyl-alpha-phenyl-1-pyrrolidineethanol hydrochloride

Product 1

HCID 40795061-Phenyl-2-(pyrrolidin-1-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A process for the preparation of [R-(R*,S*)]-β-methyl-α-phenyl-1-pyrrolidineethanol hydrochloride or its enantiomer, ##STR53## comprising the steps of: (a) refluxing (1R,2S)-(-)-norephedrine or its enantiomer, ##STR54## with 1,4-dibromobutane in the presence of a base, sodium bicarbonate and a solvent, toluene, at a reaction temperature of about 100° to about 120° C. for reaction time of about 12 to about 24 hours, while removing the water formed to give a toluene solution of crude [R-(R*,S*)]-β-methyl-α-phenyl-1-pyrrolidineethanol or its enantiomer;

Workup

  1. customwhile removing the water
  2. customformed

Sources & evidence

ORD record
ord-41089307e971488bb18d503e77f05ecd
Source dataset
uspto-grants-1999_01
Patent number
US05856492

Linked notes

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