Benzyl Bromide → methyl (2R)-1-benzyl-2-methylazetidine-2-carboxylate
Reaction equation
[CH3:1][O:2][C:3]([C@@:5]1([CH3:9])[CH2:8][CH2:7][NH:6]1)=[O:4].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH3:1][O:2][C:3]([C@@:5]1([CH3:9])[CH2:8][CH2:7][N:6]1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of (R)-2-methyl-azetidine-2-carboxylic acid methyl ester (1 eq.) in THF were added TEA (2 eq.) and benzyl bromide (1 eq.). The reaction was heated at 50° C. for 15 h. The solvent was concentrated under reduced pressure, the crude was purified by chromatography on silica gel (elution with heptane/EtOAc 1/0 to 1/1) to afford (R)-1-benzyl-2-methyl-azetidine-2-carboxylic acid methyl ester.
Workup
- concentrationThe solvent was concentrated under reduced pressure
- customthe crude was purified by chromatography on silica gel (elution with heptane/EtOAc 1/0 to 1/1)
Sources & evidence
- ORD record
- ord-0cc9d60585034281a0a48241e3e1dfc0
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759334B2
Reaction notes
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