Hydroxylamine → (-)-2-(Dimethylamino)-1-phenylethanol

HRID 1786724Notes

Reaction equation

HRID 1786724 reaction equation
[CH3:1][N:2]([CH3:12])[CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].C1([C@@H](O)CN2CCCC2)C=CC=CC=1.NO>CO>[CH3:1][N:2]([CH3:12])[CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 1208462-(Dimethylamino)-1-phenylethanolHCID 7195215HCID 7195215, compound

Product 1

HCID 120844(-)-2-(Dimethylamino)-1-phenylethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Racemic 2-dimethylamino-1-phenyl ethanol was cleaved in accordance with the 2-pyrrolidinyl-1-phenyl ethanol (see example 6) using 16.5 g of crude amino alcohol as described in example 8. The yield of oily (R)-2-dimethyl-amino-1-phenyl ethanol with a [αD20] value of −45.5° (methanol) was 8.9 g.

Sources & evidence

ORD record
ord-735eeb16aa944771b06909321c4eb700
Source dataset
uspto-grants-2009_03
Patent number
US07507827B2

Reaction notes

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