تفاعل #87120

معادلة التفاعل

(S)-tert-butyl (1-cyclopentyl-3-oxopent-4-en-2-yl)carbamate

Water

→

tert-butyl ((S)-3-cyclopentyl-1-((R)-oxiran-2-yl)-1-oxopropan-2-yl)carbamate

المردود 43.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONa bleach solution (9.50 mL, 12.8 mmol, 10% active spice) was added dropwise under nitrogen
2. 2
   استخلاصthe mixture was extracted with EtOAc (2×50 mL)
3. 3
   غسيلwashed with brine (2×50 mL)
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   تركيزconcentrated
6. 6
   أخرىThe residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=80:1)

الإجراء التجريبي

A solution of (S)-tert-butyl (1-cyclopentyl-3-oxopent-4-en-2-yl)carbamate (854 mg, 3.20 mmol) in DMF (70 mL) was cooled to −20° C. and a bleach solution (9.50 mL, 12.8 mmol, 10% active spice) was added dropwise under nitrogen. The reaction mixture was warmed to 0° C. and stirred for 1.5 h. Water (70 mL) was added and the mixture was extracted with EtOAc (2×50 mL). The organic phases were combined, washed with brine (2×50 mL), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=80:1) to afford tert-butyl ((S)-3-cyclopentyl-1-((R)-oxiran-2-yl)-1-oxopropan-2-yl)carbamate as a viscous oil (390 mg, contaminated with some impurities, 43% yield) as a yellow oil.

المصدر