2,3-Dihydrobenzofuran-5-carboxaldehyde → 3-(3-{[(2,3-Dihydro-benzofuran-5-ylmethyl)-amino]methyl}-phenyl)-propionic acid methyl ester

HRID 2117538Notes

Reaction equation

HRID 2117538 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.[O:16]1[C:20]2[CH:21]=[CH:22][C:23]([CH:25]=O)=[CH:24][C:19]=2[CH2:18][CH2:17]1>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][CH2:25][C:23]2[CH:22]=[CH:21][C:20]3[O:16][CH2:17][CH2:18][C:19]=3[CH:24]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 7359012,3-Dihydrobenzofuran-5-carboxaldehydeHCID 22282736Methyl 3-(3-(aminomethyl)phenyl)propanoate hydrochloride

Product 1

HCID 541084383-(3-{[(2,3-Dihydro-benzofuran-5-ylmethyl)-amino]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 2,3-dihydro-benzofuran-5-carbaldehyde 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 7.23 (m, 4H), 7.07 (m, 2H), 6.73 (d, 1H), 4.54 (t, 2H), 3.77 (s, 2H), 3.71 (s, 2H), 3.66 (s, 3H), 3.18 (t, 2H), 2.94 (t, 2H), 2.63 (t, 2H); MS 326 (M+1). Step B: Amide Formation

Workup

  1. temperatureat reflux over 3 h

Sources & evidence

ORD record
ord-8f7b0c64469b431288f529facc9612f4
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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