HCID 178454124, compound → HCID 178454110, compound

HRID 707286Notes

Reaction equation

HRID 707286 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:11][C@@H:10]([N:12]=[N+]=[N-])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:11][C@@H:10]([NH2:12])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 178454124HCID 178454124, compound

Product 1

HCID 178454110HCID 178454110, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of tert-butyl(cis-3-azidocyclobutyl)carbamate (7.0 g, 33.0 mmol) and palladium 10% on activated carbon (3.51 ml, 33.0 mmol, Sigma-Aldrich Chemical Company, Inc.) in three necked 1000 mL flask was flushed with N2 and closed tightly and 2M ammonia in methanol solution (200 mL) was added. The flask was evacuated and a balloon filled with hydrogen was introduced. The mixture was stirred for 18 h, filtered, and the filtrate was evaporated under reduced pressure to give the title compound, which was used in the next step without further purification.

Workup

  1. customwas flushed with N2
  2. customclosed tightly
  3. addition2M ammonia in methanol solution (200 mL) was added
  4. customThe flask was evacuated
  5. additiona balloon filled with hydrogen
  6. additionwas introduced
  7. filtrationfiltered
  8. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ceb269bfab30465c9e9f47801a99c809
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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