Hydrazine hydrate (1:1) → tert-Butyl 3-(hydrazinecarbonyl)azetidine-1-carboxylate

1-(tert-butoxycarbonyl) azetidine-3-carboxylic acid (5 g, 24.8 mmol) was suspended in dichloromethane (15 mL) and 1,1′-carbonyldiimidazole (4.56 g, 28.1 mmol) was added in portions. The resulting mixture was stirred at rt for 30 minutes and then added dropwise to a solution of hydrazine hydrate (1.94 mL, 39.9 mmol) in dichloromethane (5 mL). After the addition was complete, the mixture was stirred for 30 min at rt. The reaction mixture was washed with saturated aqueous Na2CO3 solution (2×), brine, dried (Na2SO4) and concentrated under vacuum to give a white crystalline solid, which was triturated with diethyl ether overnight, filtered and air-dried for 5 h to give a white solid.

1. additionAfter the addition
2. stirringthe mixture was stirred for 30 min at rt
3. washThe reaction mixture was washed with saturated aqueous Na2CO3 solution (2×), brine
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated under vacuum
6. customto give a white crystalline solid, which
7. customwas triturated with diethyl ether overnight
8. filtrationfiltered
9. customair-dried for 5 h
10. customto give a white solid

ORD record

ord-bbb73b5c847a4a979bfa6f46de4350f5

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957064B2