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

HRID 2283646Notes

Reaction equation

HRID 2283646 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 94.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

tert-Butyl 3-iodoazetidine-1-carboxylate (142 g, 0.50 mol) and hydrazine hydrate (245.2 mL, 5.02 mol) were mixed in ethanol (284 mL) and the reaction mixture was heated to 85° C. for 48 hours under nitrogen. The reaction mixture 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 afford the title compound as a colourless oil (88.37 g). This compound was used immediately in the next step without purification.

Workup

  1. temperatureThe reaction mixture 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-40828a2f37a74be8a4a6db05acc6768b
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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