Triethylamine → 3-{3-[(4-Isobutyl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

HRID 2117542Notes

Reaction equation

HRID 2117542 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.[CH2:16]([C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)[CH:17]([CH3:19])[CH3:18].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)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][NH:14][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:21][CH:22]=2)[CH:8]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 577537Benzaldehyde, 4-(2-methylpropyl)-HCID 5049666Sodium triacetoxyborohydrideHCID 22282736Methyl 3-(3-(aminomethyl)phenyl)propanoate hydrochloride

Product 1

HCID 542172443-{3-[(4-Isobutyl-benzylamino)-methyl]-phenyl}-propionic acid methyl esterYield 30.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(3-aminomethyl-phenyl)-propionic acid methyl ester hydrochloride salt (400 mg, 1.74 mmol), 4-isobutylbenzaldehyde (311 mg, 1.91 mmol), and triethylamine (0.26 mL, 1.91 mmol) in CH2Cl2 (4 mL) was stirred at room temperature for 4 h. Sodium triacetoxyborohydride (590 mg, 2.78 mmol) was added and the reaction was stirred for 20 h. Aqueous NaHCO3 was added and the aqueous solution was washed with CH2Cl2. The organic solution was dried (MgSO4), filtered, and concentrated. Flash chromatography (65% EtOAc in hexanes) provided the title compound of Step A (178 mg). 1H NMR (400 MHz, CDCl3) δ 7.26-7.04 (m, 8H), 3.77 (s, 2H), 3.75 (s, 2H), 3.63 (s, 3H), 2.91 (t, 2H), 2.60 (t, 2H), 2.41 (d, 2H), 1.80 (m, 1H), 0.85 (m, 6H); MS 340 (M+1).

Workup

  1. washthe aqueous solution was washed with CH2Cl2
  2. dry with materialThe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-16ee4784af674d67998a35a972c17832
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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