Ethyl bromoacetate → 2-[2-{N-(t-butoxycarbonyl)-N-(ethoxycarbonylmethyl)amino}ethyl]pyridine

HRID 1647146Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].[Cl-].[NH4+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-[2-(t-butoxycarbonylamino)ethyl]pyridine (2 g) in dimethylformamide (10 ml) was added to a suspension of sodium hydride (0.54 g) in dimethylformamide (10 ml) at 0° C. The mixture was stirred at 0° C. for 1 hour and at room temperature for 1 hour. Then a solution of ethyl bromoacetate (1.5 ml) in dimethylformamide (5 ml) was added thereto, and the mixture was stirred at room temperature for 2 hours. The solution was poured into saturated ammonium chloride (50 ml) and the mixture was extracted with ethyl acetate (30 ml×2). The combined organic layer was washed with saturated sodium chloride solution, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified with silica gel column chromatography (MeOH:CHCl3 =1:99 as an eluent) to give 2-[2-{N-(t-butoxycarbonyl)-N-(ethoxycarbonylmethyl)amino}ethyl]pyridine.

Workup

stirringthe mixture was stirred at room temperature for 2 hours
extractionthe mixture was extracted with ethyl acetate (30 ml×2)
washThe combined organic layer was washed with saturated sodium chloride solution
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified with silica gel column chromatography (MeOH

Sources & evidence

ORD record: ord-5eabb2b29b064e01ba5696ef118cc409
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05430022

Reaction notes

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