4-tert-Butylbenzaldehyde → 3-{3-[(4-tert-Butyl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

HRID 2117535Notes

Reaction equation

HRID 2117535 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][NH2:14])[CH:8]=1.[C:16]([C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>CO>[CH3:2][O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][NH:14][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:21][CH:22]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 703244-tert-ButylbenzaldehydeHCID 22282736Methyl 3-(3-(aminomethyl)phenyl)propanoate hydrochloride

Product 1

HCID 543643433-{3-[(4-tert-Butyl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound of Step A was prepared from 3-(3-aminomethyl-phenyl)-propionic acid methyl ester hydrochloride salt, of Preparation 44, and 4-tert-butyl-benzaldehyde using the method described in Example 1, Step A except the imine was formed in MeOH at reflux over 3 h. 1H NMR (400 MHz, CDCl3) δ 7.35 (m, 2H), 7.25 (m, 2H), 7.18 (m, 2H), 7.08 (d, 1H), 3.79 (s, 2H), 3.77 (s, 2H), 3.66 (s, 3H), 2.94 (t, 2H), 2.63 (t, 2H), 1.31 (s, 9H); MS 340 (M+1).

Workup

  1. temperatureat reflux over 3 h

Sources & evidence

ORD record
ord-ca613e4d31a54a779d496abc858d1ec8
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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