Hydrazine hydrate (1:1) → Tert-butyl 3-hydrazinylazetidine-1-carboxylate

HRID 1619649Notes

Reaction equation

HRID 1619649 reaction equation
CS(O[CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)(=O)=O.O.[NH2:18][NH2:19]>O>[NH:18]([CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)[NH2:19]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

Product 1

HCID 58042291Tert-butyl 3-hydrazinylazetidine-1-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A suspension of tert-butyl 3-[(methylsulfonyl)oxy]azetidine-1-carboxylate (Preparation 35, 7.11 g, 28.3 mmol) in neat hydrazine monohydrate (13.7 mL, 283 mmol) was heated to 95° C. for 18 hours. The reaction was cooled to room temperature, then water (100 mL) was added and the mixture extracted with dichloromethane (5×100 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a the title compound as a clear oil (4.71 g, 89%). The compound was used without further purification in the next step.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionthe mixture extracted with dichloromethane (5×100 mL)
  3. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bcc8803a471b4cbcac9df4a0f67c32b9
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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