반응 #794434
ord-000d153fb43b4072aa2b83035a5640a2
반응 방정식
반응물
시약
반응 조건
후처리
- 1온도cooled in an acetone/ice bath under nitrogen
- 2기타The reaction was partitioned between water (200 mL), saturated ammonium chloride (50 mL) and dichloromethane (100 mL)
- 3추출The aqueous was extracted with additional dichloromethane (100 mL)
- 4건조They were dried with magnesium sulfate
- 5기타evaporated to dryness under reduced pressure
- 6기타using a 40° C.
- 7온도As the mixture warmed it
- 8기타the flask was fitted with a reflux condenser
- 9온도The bath temperature was raised to 95° C
- 10기타After an additional 3 hours the solution was evaporated to dryness under reduced pressure
실험 절차
Benzyl (cis-3-hydroxycyclobutyl)carbamate (intermediate 47, 3.26 g, 14.73 mmol) was suspended in a mixture of diisopropylethylamine (4 ml, 23.00 mmol) and dichloromethane (100 mL) and cooled in an acetone/ice bath under nitrogen. Methanesulfonyl chloride (1.3 ml, 16.80 mmol) was added slowly and the solution stirred for minutes. The reaction was partitioned between water (200 mL), saturated ammonium chloride (50 mL) and dichloromethane (100 mL). The aqueous was extracted with additional dichloromethane (100 mL) and the organic layers combined. They were dried with magnesium sulfate and evaporated to dryness under reduced pressure using a 40° C. water bath. The crude solid mesylate was suspended in ethanol (10 mL) and treated with hydrazine (anhydrous, 4 ml, 127 mmol). The slurry was heated at 80° C. As the mixture warmed it became homogeneous. After 2 hours additional hydrazine (2 mL) was added and the flask was fitted with a reflux condenser. The bath temperature was raised to 95° C. After an additional 3 hours the solution was evaporated to dryness under reduced pressure to give benzyl (trans-3-hydrazinylcyclobutyl)carbamate as a thick white oil. It was further dried under high vacuum at 50° C. for 20 minutes then used without further purification.