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

HRID 85314Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][NH:16][CH2:17][CH2:18][OH:19])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][NH:16][CH2:17][CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Next, to toluene (50 ml) were added 2-[(3-benzyloxyphenyl)methylamino]ethanol (10.3 g, 39.9 mmol), pivaloyl chloride (9.6 g, 79.8 mmol), and pyridine (7.6 g, 95.8 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-benzyloxyphenyl)methylamino]ethyl ester as a colorless oily matter (yield: 8.9 g (65.1%)).

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-bda2e86674814a16a9803aff82f02b5b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846955B2

Reaction notes

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