tert-Butyl bromoacetate → (1-Tert-butoxycarbonylmethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl)-acetic acid methyl ester

HRID 851932Notes

Reaction equation

HRID 851932 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:15].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:6]1=[O:15]

Participants

3

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 21519358Methyl 2-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetate

Product 1

HCID 69008131(1-Tert-butoxycarbonylmethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl)-acetic acid methyl esterYield 89%

Procedure

Following a similar N-alkylation procedure described in example 6, the (2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl)-acetic acid methyl ester (0.99 mmol) is alkylated with tert-butyl bromoacetate to give (1-tert-butoxycarbonylmethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl)-acetic acid methyl ester as a colorless oil, after purification by silica gel chromatography (hexane/EtOAc). Yield: 89%. MS: (ES+): 356.2 [M+23].

Sources & evidence

ORD record
ord-fcfe85a4540744cc900bfbe57f3352f8
Source dataset
uspto-grants-2007_08
Patent number
US07253164B2

Reaction notes

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