Methyl 1-(methyl{[(phenylmethyl)oxy]carbonyl}amino)cyclopropanecarboxylate → Methyl 1-(methylamino)cyclopropane-1-carboxylate

HRID 1366571Notes

Reaction equation

HRID 1366571 reaction equation
[CH3:1][N:2](C(OCC1C=CC=CC=1)=O)[C:3]1([C:6]([O:8][CH3:9])=[O:7])[CH2:5][CH2:4]1>CO>[CH3:1][NH:2][C:3]1([C:6]([O:8][CH3:9])=[O:7])[CH2:5][CH2:4]1

Participants

3

Reactant 1

HCID 66936097Methyl 1-(methyl{[(phenylmethyl)oxy]carbonyl}amino)cyclopropanecarboxylate

Product 1

HCID 13556583Methyl 1-(methylamino)cyclopropane-1-carboxylateYield 45.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-(methyl{[(phenylmethyl)oxy]carbonyl}amino)cyclopropanecarboxylate (assumed 6.8 g, 25.91 mmol, 100% theoretical yield) was dissolved in 30 mL of MeOH, degassed and placed under argon. 10% Pd/C (2.04 g) was added, and the contents were thoroughly degassed and placed under a hydrogen balloon overnight. The contents were then degassed, and the Pd/C was removed by filtration through Celite, washing with MeOH. The filtrate was concentrated in vacuo to provide pure methyl 1-(methylamino)cyclopropanecarboxylate (1.53 g, 45% over two step). LCMS: (M+H)+: 130.1.

Workup

  1. customdegassed
  2. addition10% Pd/C (2.04 g) was added
  3. customthe contents were thoroughly degassed
  4. customballoon overnight
  5. customThe contents were then degassed
  6. customthe Pd/C was removed by filtration through Celite
  7. washwashing with MeOH
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9748c317dcf1473da7c80fcc3dbf7f04
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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