Ammonium Acetate → Ethyl (5R)-2-amino-5-methyl-1-cyclopentene-1-carboxylate

HRID 80995Notes

Reaction equation

HRID 80995 reaction equation
C([O-])(=O)C.[NH4+:5].[CH3:6][CH:7]1[CH2:11][CH2:10][C:9](=O)[C@@H:8]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]>CO>[NH2:5][C:9]1[CH2:10][CH2:11][C@@H:7]([CH3:6])[C:8]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 86618740(R)-ethyl 2-methyl-5-oxocyclopentanecarboxylate

Product 1

HCID 59671147Ethyl (5R)-2-amino-5-methyl-1-cyclopentene-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ammonium acetate (240.03 g, 3113.9 mmol) was added to a solution of (R)-ethyl 2-methyl-5-oxocyclopentanecarboxylate (106.0 g, 622.78 mmol) in MeOH (1.2 L). The reaction mixture was stirred at room temperature under nitrogen for 20 hours, after which it was complete as judged by TLC and HPLC. The reaction mixture was concentrated to remove MeOH. The resulting residue was dissolved in DCM, washed twice with H2O, once with brine, dried (Na2SO4), filtered, and concentrated to give (R)-ethyl 2-amino-5-methylcyclopent-1-enecarboxylate (102 g, 97% yield) as an oil. LC/MS (APCI+) m/z 170 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove MeOH
  3. dissolutionThe resulting residue was dissolved in DCM
  4. washwashed twice with H2O, once with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8424087ad2964ac8b9f9c92003b78a61
Source dataset
uspto-grants-2014_09
Patent number
US08846683B2

Reaction notes

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