Ammonium Chloride → (S)-1-Benzyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate
Reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[CH3:7][O:8][C:9](=[O:26])[C@@H:10]1CC(=O)C[N:11]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].[Cl-].[NH4+]>C(OCC)C.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:7][O:8][C:9](=[O:26])[C@@H:10]1[CH2:3][C:2](=[CH2:5])[CH2:1][N:11]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
Potassium t-butoxide (1.41 g, 12.6 mmol) was suspended in diethyl ether (100 ml). To the suspension was added methyltriphenylphosphonium bromide (4.80 g, 13.4 mmol), and the resulting mixture was stirred at 5° C. for 15 minutes. To the mixture was added (S)-1-benzyloxycarbonyl-4-oxoproline methyl ester (2.50 g, 9.0 mmol) in diethyl ether (30 ml), and the resulting mixture was stirred at 35° C. for 3 hours. At the end of this time, the reaction mixture was added to a saturated solution of ammonium chloride (50 ml) under ice cooling, and then partitioned. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent, ethyl acetate:hexane=1:3), to give the title compound (1.80 g) as a pale yellow oil (yield 72%).
Workup
- stirringthe resulting mixture was stirred at 35° C. for 3 hours
- custompartitioned
- washThe organic layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was removed by distillation under reduced pressure
- customThe residue was purified by column chromatography through silica gel (eluent, ethyl acetate:hexane=1:3)
Sources & evidence
- ORD record
- ord-3b056c8ed15b41ed951feb84fb0fb850
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091352B2
Reaction notes
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