HCID 71280019, compound → tert-Butyl [(1-aminocyclopropyl)methyl]carbamate

HRID 246710Notes

Reaction equation

HRID 246710 reaction equation
C(OC(=O)[NH:10][C:11]1([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH2:12]1)C1C=CC=CC=1>CO.[Pd]>[NH2:10][C:11]1([CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 71280019HCID 71280019, compound

Product 1

HCID 68451901tert-Butyl [(1-aminocyclopropyl)methyl]carbamateYield 75.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of [1-(tert-butoxycarbonylamino-methyl)-cyclopropyl]-carbamic acid benzyl ester (0.912 g, 2.85 mmol) in 120 mL of methanol was added 10% Pd on carbon (200 mg) in one portion at room temperature. Then the mixture was degassed by bubbling hydrogen for 5 minutes then stirred under a hydrogen atmosphere at room temperature for 16 hours. The mixture was filtered to remove the catalyst and the filtrate was evaporated at 40° C. under reduced pressure to give tert-butyl (1-aminocyclopropyl)methylcarbamate (0.4 g, 75.4%) as a colorless oil which was used into next step without further purification. MS: (M+H)+=187.2.

Workup

  1. customThen the mixture was degassed
  2. customby bubbling hydrogen for 5 minutes
  3. filtrationThe mixture was filtered
  4. customto remove the catalyst
  5. customthe filtrate was evaporated at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-4b2b2e3497914e8d8e13ab486ffeaa5e
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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