7-Methoxy-3,4-dihydroquinolin-2(1H)-one → 3-(7-methoxy-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethyl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 1890438Notes

Reaction equation

HRID 1890438 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.[C:14]([O:18][C:19]([N:21]1[CH2:24][CH:23]([CH2:25]OS(C)(=O)=O)[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>>[C:14]([O:18][C:19]([N:21]1[CH2:24][CH:23]([CH2:25][N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH2:7][CH2:8][C:9]2=[O:13])[CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

3

Reactant 2

HCID 128994187-Methoxy-3,4-dihydroquinolin-2(1H)-oneHCID 21959416Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylate

Product 1

HCID 671309053-(7-methoxy-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethyl)-azetidine-1-carboxylic acid tert-butyl esterYield 71%

Procedure

Using the procedure of Example 2, step 2.i, but starting from 3,4-dihydro-7-methoxy-2(1H)-quinolinone (prepared according to WO 2006/134378; 886 mg) and 3-[[(methylsulfonyl)oxy]methyl]-1-azetidinecarboxylic acid tert-butyl ester (1459 mg; prepared according to WO 02/066470), the title compound was isolated as a colourless oil (1223 mg; 71% yield).

Sources & evidence

ORD record
ord-eff5ee2b9e65422184cc2fe04e7d37c3
Source dataset
uspto-grants-2013_08
Patent number
US08507478B2

Reaction notes

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