HCID 178454124, compound → HCID 178454110, compound

HRID 707425Notes

Reaction equation

HRID 707425 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, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of tert-butyl(cis-3-azidocyclobutyl)carbamate (15.00 g, 70.7 mmol) and palladium 10 wt. % (dry basis) on activated carbon, wet (3.76 ml, 35.3 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 (11.1 g, 59.6 mmol, 84% yield), 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-0aaa1f83639240048bd3ae9ccf498850
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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