تفاعل #794434
ord-000d153fb43b4072aa2b83035a5640a2
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المعالجة
- 1درجة الحرارةcooled in an acetone/ice bath under nitrogen
- 2أخرىThe reaction was partitioned between water (200 mL), saturated ammonium chloride (50 mL) and dichloromethane (100 mL)
- 3استخلاصThe aqueous was extracted with additional dichloromethane (100 mL)
- 4تجفيفThey were dried with magnesium sulfate
- 5أخرىevaporated to dryness under reduced pressure
- 6أخرىusing a 40° C.
- 7درجة الحرارةAs the mixture warmed it
- 8أخرىthe flask was fitted with a reflux condenser
- 9درجة الحرارةThe bath temperature was raised to 95° C
- 10أخرىAfter an additional 3 hours the solution was evaporated to dryness under reduced pressure
الإجراء التجريبي
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.