2-Butoxy-4-formyl-benzoic Acid Methyl Ester → 2-Butoxy-4-({[4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amino}-methyl)-benzoic Acid Methyl Ester

HRID 424808Notes

Reaction equation

HRID 424808 reaction equation
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH3:14])=[C:9]([CH3:15])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][C:20](=[O:34])[C:21]1[CH:26]=[CH:25][C:24]([CH:27]=O)=[CH:23][C:22]=1[O:29][CH2:30][CH2:31][CH2:32][CH3:33].COC(=O)C1C=CC(CN(C2C=CC(O[Si](C(C)(C)C)(C)C)=CC=2C)C)=CC=1C>>[CH3:18][O:19][C:20](=[O:34])[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][N:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][Si:5]([C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:17])[CH3:16])=[CH:8][C:9]=2[CH3:15])[CH3:14])=[CH:23][C:22]=1[O:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 3

HCID 574433192-Butoxy-4-formyl-benzoic Acid Methyl EsterHCID 667041204-[(tert-butyldimethylsilyl)oxy]-N,2-dimethylanilineHCID 667041694-({[4-(Tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amino}-methyl)-2-methyl-benzoic acid methyl ester

Product 1

HCID 667041812-Butoxy-4-({[4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amino}-methyl)-benzoic Acid Methyl Ester

Procedure

The title compound is prepared by reductive amination of [4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amine with 2-butoxy-4-formyl-benzoic acid methyl ester, essentially as described in the synthesis of 4-({[4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amino}-methyl)-2-methyl-benzoic acid methyl ester using the appropriate starting material. The title compound is obtained as syrup after workup. LC-ES/MS m/e 472.3 (M+1).

Sources & evidence

ORD record
ord-0d21f20779364c87894f4c8590f3927a
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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