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

HRID 527216Notes

Reaction equation

HRID 527216 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 orange 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-5eeec2f3a98c4c9b95dc1a1abd9b3ced
Source dataset
uspto-grants-2016_05
Patent number
US09346789B2

Reaction notes

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