HCID 178454124, compound → HCID 178454110, compound

HRID 707264Notes

Reaction equation

HRID 707264 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 99.2%

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) in a three necked 1000 mL flask was flushed with nitrogen 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 at room temperature for 18 h, filtered, and the filtrate was evaporated under reduced pressure to give the desired product tert-butyl(cis-3-aminocyclobutyl)carbamate (6.1 g, 99% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.64 (br. s., 1 H), 3.72 (d, J=6.85 Hz, 1 H), 3.12 (t, J=7.73 Hz, 1 H), 2.71 (d, J=7.24 Hz, 2 H), 1.51 (q, J=9.85 Hz, 2 H), 1.43 (br. s., 11 H).

Workup

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

Sources & evidence

ORD record
ord-adeca629a6e6467e85bb920ba0798b5e
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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