Hydrazine → HCID 178514375, compound

Temperature

80 °C

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.

1. temperaturecooled in an acetone/ice bath under nitrogen
2. customThe reaction was partitioned between water (200 mL), saturated ammonium chloride (50 mL) and dichloromethane (100 mL)
3. extractionThe aqueous was extracted with additional dichloromethane (100 mL)
4. dry with materialThey were dried with magnesium sulfate
5. customevaporated to dryness under reduced pressure
6. customusing a 40° C.
7. temperatureAs the mixture warmed it
8. customthe flask was fitted with a reflux condenser
9. temperatureThe bath temperature was raised to 95° C
10. customAfter an additional 3 hours the solution was evaporated to dryness under reduced pressure

ORD record

ord-000d153fb43b4072aa2b83035a5640a2

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174992B2