Benzyl Bromide → HCID 70564348, compound
Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:8][CH2:7][N:6]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:4].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CCCCCC.[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:8][CH2:7][N:6]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:4]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
To a solution of azetidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1 eq.) in dry THF under Argon at −78° C. was added a solution of LiHMDS 1M in hexane (1.3 eq.). The mixture was stirred at −78° C. for 1 h, then benzyl bromide (1.3 eq.) was added. The reaction was stirred at −78° C. for 30 min, then at 0° C. for 2 h, then at 20° C. for 1 h. The crude was diluted with EtOAc, carefully hydrolyzed with a saturated aqueous solution of NH4Cl. The organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 98/2 to 80/20) to afford 2-benzyl-azetidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester.
Workup
- stirringThe reaction was stirred at −78° C. for 30 min
- waitat 0° C. for 2 h
- waitat 20° C. for 1 h
- washThe organic layer was washed with water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 98/2 to 80/20)
Sources & evidence
- ORD record
- ord-920fcf7c4cf84573a964ea9bbc87fd21
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759334B2
Reaction notes
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