Methyl 2-oxo-3-phenylpropanoate → (3S,5S,6S)-3,6-dibenzyl-5-hydroxypiperidin-2-one

HRID 1743067Notes

Reaction equation

HRID 1743067 reaction equation
CO[C:3](=[O:13])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5].[CH3:14]C(C)C(=O)C(OC)=O.[C:23]1([CH2:29][C:30](=O)[C:31]([O:33]C)=O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:29]([C@H:30]1[CH2:14][C@H:3]([OH:13])[C@H:4]([CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:5][C:31]1=[O:33])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 562359Methyl 2-oxo-3-phenylpropanoateHCID 736234L-Phenylalanine, methyl esterHCID 12449855Methyl 3-methyl-2-oxobutanoate

Product 1

HCID 57041890(3S,5S,6S)-3,6-dibenzyl-5-hydroxypiperidin-2-one

Procedure

Following the procedures outlined in Examples 2-6, and replacing L-cylohexylalanine methyl ester with L-phenylalanine methyl ester in Example 2 and methyl 3-methyl-2-oxobutyrate with methyl 3-phenyl-2-oxopropionate in Example 4 provides the title compound.

Sources & evidence

ORD record
ord-e30f174db4a347a1a509a46170e82540
Source dataset
uspto-grants-1994_08
Patent number
US05342981

Reaction notes

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