Phenylpropanolamine → (1S,2R)-2-amino-1-phenylpropan-1-ol

HRID 381651Notes

Reaction equation

HRID 381651 reaction equation
[CH3:1][C@H:2]([NH2:11])[C@H:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[BH4-].[Na+]>C(O)C>[CH3:1][C@@H:2]([NH2:11])[C@@H:3]([OH:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 10297PhenylpropanolamineHCID 4311764Sodium borohydride

Product 1

HCID 26934(1S,2R)-2-amino-1-phenylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

As shown in the scheme above, (1R, 2S)-(−)-norephedrine is reacted with an optionally substituted benzaldehyde by refluxing in ethanol, and reducing the product of that reaction with sodium borohydride at ambient temperature to produce the desired norephedrine derivative compound.

Sources & evidence

ORD record
ord-1d749c0eef934d3cbcb4053555977afb
Source dataset
uspto-grants-2001_10
Patent number
US06307048B1

Reaction notes

Loading…