Ammonia → HCID 178453653, compound

HRID 577742Notes

Reaction equation

HRID 577742 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C@H:9]1[CH2:12][C@H:11]([N:13]=[N+]=[N-])[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[H][H].N.CCOC(C)=O>CO.[Pd]>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C@H:9]1[CH2:10][C@H:11]([NH2:13])[CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 178418361HCID 178418361, compoundHCID 178453654HCID 178453654, compound

Product 1

HCID 178453653HCID 178453653, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To the mixture of tert-butyl(trans-3-azidocyclobutyl)methylcarbamate (1.8 g, 7.95 mmol) and Pd/C (200 mg) in MeOH (5 mL) under hydrogen atmosphere (hydrogen balloon) was added NH3(g)/MeOH (saturated, 50 mL) via syringe. The resulting mixture was stirred at rt for three hours until TLC analysis (EtOAc:petroleum ether=1:2) showed the reaction was complete. Pd/C was filtered off and the resulting solution was concentrated and dried in vacuum to afford crude title compound (1.6 g), which was used for the next steps without further purification.

Workup

  1. filtrationPd/C was filtered off
  2. concentrationthe resulting solution was concentrated
  3. customdried in vacuum

Sources & evidence

ORD record
ord-a11b00fae2de4b68a5c1ed124bb08c80
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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