Hydrazine → HCID 178454123, compound

HRID 707329Notes

Reaction equation

HRID 707329 reaction equation
CS(O[C@H:6]1[CH2:9][C@@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)(=O)=O.C(OC(=O)N[C@H]1C[C@H](N)C1)(C)(C)C.[NH2:31][NH2:32]>C(O)C>[C:14]([O:13][C:11](=[O:12])[NH:10][C@H:8]1[CH2:9][C@H:6]([NH:31][NH2:32])[CH2:7]1)([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 178454111HCID 178454111, compoundHCID 178454135HCID 178454135, compound

Product 1

HCID 178454123HCID 178454123, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

Cis-3-((tert-butoxycarbonyl)amino)cyclobutyl methanesulfonate (intermediate in the synthesis of tert-butyl(trans-3-aminocyclobutyl)carbamate from Radchenko, D. S., Pavlenko, S. O., et al J. Org. Chem. 2010, 75, 5941-5952, 10 g, 37.7 mmol) and hydrazine (anhydrous, 5 ml, 159 mmol) were added to ethanol (100 mL) and scaled in a pressure vessel. The mixture was heated at 130° C. for 1½ hours. The crude was evaporated to dryness under reduced pressure. Purification using silica chromatography (0-10% (2 N ammonia in methanol) in dichloromethane gradient, visualize with iodine chamber) gave the desired tert-butyl(trans-3-hydrazinylcyclobutyl)carbamate (4.1 g, 20.37 mmol, 54.0% yield).

Workup

  1. customscaled in a pressure vessel
  2. customThe crude was evaporated to dryness under reduced pressure
  3. customPurification

Sources & evidence

ORD record
ord-aa5bdea73a344884a240fb8eebbfbfff
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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