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

HRID 1595956

Reaction equation

HRID 1595956 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-b28c151d057f4f0bbcfc10c69ab8201e
Source dataset
uspto-grants-2001_09
Patent number
US06288233B1

Linked notes

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