Ethyl 5-methyl-3-oxohexanoate → Ethyl 3-amino-5-methylhexanoate

HRID 1865314Notes

Reaction equation

HRID 1865314 reaction equation
[CH3:1][CH:2]([CH3:12])[CH2:3][C:4](=O)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C([O-])(=O)C.[NH4+:17]>C(O)C>[NH2:17][CH:4]([CH2:3][CH:2]([CH3:12])[CH3:1])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 2

HCID 96344Ethyl 5-methyl-3-oxohexanoateHCID 517165Ammonium Acetate

Product 1

HCID 17788054Ethyl 3-amino-5-methylhexanoateYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Ru(OCOCH3)2((R)-dm-binap)(5.5 mg, 0.058 mmol), ethyl 5-methyl-3-oxo-hexanoate (500 mg, 2.903 mmol), ammonium acetate (224 mg, 2.903 mmol) and ethanol (2.5 mL) were placed in a 2.5 mL-stainless autoclave under atmosphere of nitrogen, and the mixture was further stirred under a hydrogen pressure of 3 MPa at 80° C. for 15 hours. After completion of the reaction, the solvent was removed by evaporation in vacuo and the residue was purified by column chromatography on silica gel (eluent:hexane ethyl acetate/triethylamine=50/50/5) to give ethyl (−)-3-amino-5-methylhexanoate (175 mg) as a colorless oil in 35.0% yield. The resulting ethyl (−)-3-amino-5-methylhexanoate was converted into ethyl 3-(4-nitrobenzoylamino)-5-methylhexanoate, and the enantiomeric excess of the product was found to be 97.3% ee by HPLC analysis using a CHIRALCEL OD-H column.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by evaporation in vacuo
  3. customthe residue was purified by column chromatography on silica gel (eluent:hexane ethyl acetate/triethylamine=50/50/5)

Sources & evidence

ORD record
ord-4cfaf528d50a42728553f1f8033395d4
Source dataset
uspto-grants-2009_12
Patent number
US07626034B2

Reaction notes

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