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

HRID 46379Notes

Reaction equation

HRID 46379 reaction equation
I[CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.O.[NH2:14][NH2:15]>C(O)C>[NH:14]([CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1)[NH2:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylate

Product 1

HCID 58042291Tert-butyl 3-hydrazinylazetidine-1-carboxylateYield 94.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Tert-butyl 3-iodoazetidine-1-carboxylate (142 g, 0.5016 mol) and hydrazine hydrate (245.21 mL, 5.02 mol) were mixed in ethanol (284 mL) and the reaction was heated to 85° C. for 48 hours under nitrogen. The reaction was cooled and the ethanol was removed in vacuo. The residue was partitioned between water (200 mL) and dichloromethane (300 mL), the water layer was re-extracted with dichloromethane (2×200 mL), the combined organics were dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the title compound as a colourless oil, (88.37 g). This compound was used immediately in the next step.

Workup

  1. temperatureThe reaction was cooled
  2. customthe ethanol was removed in vacuo
  3. customThe residue was partitioned between water (200 mL) and dichloromethane (300 mL)
  4. extractionthe water layer was re-extracted with dichloromethane (2×200 mL)
  5. dry with materialthe combined organics were dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5577703fce0f4d248910d660cacfb4f5
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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