反応 #9987

反応方程式

Potassium t-butoxide

(S)-1-benzyloxycarbonyl-4-oxoproline methyl ester

ammonium chloride

→

title compound

収率 72.6%

(S)-1-Benzyloxycarbonyl-4-methylideneproline methyl ester

収率 72.6%

溶媒

diethyl ether

diethyl ether

反応条件

後処理

1. 1
   workup.STIRRINGthe resulting mixture was stirred at 35° C. for 3 hours
2. 2
   その他partitioned
3. 3
   洗浄The organic layer was washed with water
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   その他the solvent was removed by distillation under reduced pressure
6. 6
   その他The residue was purified by column chromatography through silica gel (eluent, ethyl acetate:hexane=1:3)

実験手順

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%).

出典