Pyridine → 2,2-Dimethylpropionic acid 2-[(3-methoxyphenyl)methylamino]ethyl ester

HRID 85308Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][NH:10][CH2:11][CH2:12][OH:13])[CH:6]=[CH:7][CH:8]=1.[C:14](Cl)(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16].N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][NH:10][CH2:11][CH2:12][O:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Next, in toluene (100 ml) were added 2-[(3-methoxyphenyl)methylamino]ethanol (8.1 g), pivaloyl chloride (10.8 g, 89.4 mmol), and pyridine (8.5 g, 107 mmol). The mixture was stirred at room temperature for 1 hour and further at 85° C. for 2 hours. After pyridine hydrochloride was removed by filtration, the filtrate was concentrated. The product was purified by silica gel chromatography to give 2,2-dimethylpropionic acid 2-[(3-methoxyphenyl)methylamino]ethyl ester as a colorless oily matter (yield: 10.4 g (78.4%)).

Workup

customAfter pyridine hydrochloride was removed by filtration
concentrationthe filtrate was concentrated
customThe product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-17b473f00de84cd2994e2ce66ff4f174
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846955B2

Reaction notes

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