Methyl 5-methyl-3-oxohexanoate → HCID 86036461, compound

HRID 1865313Notes

Reaction equation

[CH3:1][CH:2]([CH3:11])[CH2:3][C:4](=O)[CH2:5][C:6]([O:8][CH3:9])=[O:7].C([O-])(=O)C.[NH4+:16]>CO>[C:6]([OH:8])(=[O:7])[CH3:5].[NH2:16][CH:4]([CH2:3][CH:2]([CH3:11])[CH3:1])[CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 80 °C

Procedure

Ru(OAc)2((R)-dm-binap) (0.201 g, 0.211 mmol), methyl 5-methyl-3-oxohexanoate (10.00 g, 63.2 mmol), ammonium acetate (5.02 g, 63.2 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 24 hours. After completion of the reaction, the solvent was removed by evaporation to give methyl (−)-3-amino-5-methylhexanoate acetate as a crude material (12.70 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-5-methylhexanoate was 74.4%. The enantiomeric excess of methyl (−)-3-amino-5-methylhexanoate in the crude product was determined to be 97.7% ee by HPLC analysis using a SUMICHIRAL OA-4100R column after conversion into methyl 3-(4-nitrobenzoylamino)-5-methylhexanoate.

Workup

customAfter completion of the reaction
customthe solvent was removed by evaporation

Sources & evidence

ORD record: ord-ae4a6215edc0483ca66c274951b77e00
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07626034B2

Reaction notes

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