Ammonium Acetate → HCID 85961599, compound

HRID 1865315Notes

Reaction equation

HRID 1865315 reaction equation
O=[C:2]([CH:8]([CH3:10])[CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C([O-])(=O)C.[NH4+:15]>CO>[C:4]([OH:6])(=[O:5])[CH3:3].[NH2:15][CH:2]([CH:8]([CH3:10])[CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 2759969Methyl 4-methyl-3-oxopentanoate

Product 1

HCID 85961599HCID 85961599, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Ru(OAc)2((R)-dm-binap) (0.221 g, 0.231 mmol), methyl 3-oxo-4-methylpentanoate (10.00 g, 69.4 mmol), ammonium acetate (5.52 g, 69.4 mmol) and methanol (50 mL) were placed in a 100 mL stainless steel autoclave under nitrogen atmosphere, and then the mixture was stirred under a hydrogen pressure of 3 MPa at 80° C. for 67 hours. After completion of the reaction, the solvent was removed by evaporation to give methyl (−)-3-amino-4-methylpentanoate acetate as a crude material (11.42 g). The crude product was treated with 7N ammonia/methanol and analyzed by GLC using a capillary column TC-5HT, indicating that the yield of methyl (−)-3-amino-4-methylpentanoate was 85.7%. The enantiomeric excess of methyl (−)-3-amino-4-methylpentanoate in the crude product was determined to be 97.8% ee by HPLC analysis using a SUMICHIRAL OA-4100R column after conversion into methyl 3-(4-nitrobenzoylamino)-4-methylpentanoate.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-92b5c97d786f4289aac739d1d95216be
Source dataset
uspto-grants-2009_12
Patent number
US07626034B2

Reaction notes

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