Water → (2r)-3-Aza-2-phenyl-4-(3,5-dimethylphenyl)but-3-en-1-ol

HRID 507786Notes

Reaction equation

HRID 507786 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[CH:5]=O.C1C=CC([CH:17]([NH2:20])CO)=CC=1.[OH2:21].[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:27]1([C@@H:22]([CH:28]=[CH:5][C:4]2[CH:3]=[C:2]([CH3:1])[CH:9]=[C:8]([CH3:10])[CH:7]=2)[CH2:23][OH:21])[CH:26]=[CH:25][CH:24]=[N:20][CH:17]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 34225Benzaldehyde, 3,5-dimethyl-HCID 924662-Amino-2-phenylethanol

Product 1

HCID 68464252(2r)-3-Aza-2-phenyl-4-(3,5-dimethylphenyl)but-3-en-1-ol

Procedure

A solution of 3,5-dimethylbenzaldehyde (30.0 g) and (R)-phenylglycinol (30.7 g) in toluene (200 ml) was refluxed for 3 hours with removing water. The reaction solution was concentrated to give the title compound (59.7 g) having the following physical data.

Workup

  1. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-4f181c044fb94d2fad5acf4989f8d97a
Source dataset
uspto-grants-2010_08
Patent number
US07786161B2

Reaction notes

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