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

HRID 911818Notes

Reaction equation

HRID 911818 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][C:4](=O)[C@@H:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].C([O-])(=O)C.[NH4+:17]>CO>[NH2:17][C:4]1[CH2:5][CH2:6][C@@H:2]([CH3:1])[C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

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

To a solution of (R)-ethyl 2-methyl-5-oxocyclopentanecarboxylate (106 g, 622 mmol) in 1.2 L MeOH was added ammonium acetate (240 g, 3.1 mol). The reaction was stirred for 20 hours and concentrated to remove MeOH. The resulting residue was dissolved in CH2Cl2, washed with H2O, brine, dried (Na2SO4), filtered and concentrated to give the title compound (102 g, 97% yield) as an orange oil.

Workup

  1. concentrationconcentrated
  2. customto remove MeOH
  3. dissolutionThe resulting residue was dissolved in CH2Cl2
  4. washwashed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bd0311f2c544423dbe1842a5ce7d3497
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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