P-Hydroxynorephedrine → ethyl 2-[2-bromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetate

HRID 1862629Notes

Reaction equation

HRID 1862629 reaction equation
[NH2:1][C@@H:2]([CH3:12])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[OH:4].[Br:13][C:14]1[CH:26]=[C:25]([CH2:27][CH2:28]Br)[CH:24]=[CH:23][C:15]=1[O:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CN(C)C=O>[Br:13][C:14]1[CH:26]=[C:25]([CH2:27][CH2:28][NH:1][C@@H:2]([CH3:12])[C@H:3]([OH:4])[C:5]2[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=2)[CH:24]=[CH:23][C:15]=1[O:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

4

Reactant 2

HCID 6931143P-HydroxynorephedrineHCID 15895328Ethyl 2-[2-bromo-4-(2-bromoethyl)phenoxy]acetate

Product 1

HCID 15895329ethyl 2-[2-bromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetateYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of (1R,2S)-2-amino-1-(4-hydroxyphenyl)propan-1-ol (475 mg), ethyl 2-[2-bromo-4-(2-bromoethyl)phenoxy]acetate (520 mg) and molecular sieves 4A powder (1.42 g) in N,N-dimethylformamide (4.7 ml) was stirred for 2 days at room temperature. Purification of the reaction mixture by medium pressure liquid column chromatography on aminopropyl silica gel (eluent:dichloromethane/methanol=10/1) gave ethyl 2-[2-bromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetate (356 mg).

Workup

  1. customPurification of the reaction mixture by medium pressure liquid column chromatography on aminopropyl silica gel (eluent:dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-ef43e156f97c48b3a824f08e8ee18019
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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