HCID 67788598, compound → 1-(Phenylmethyl) (2S)-5-oxo-1,2-piperidinedicarboxylate

HRID 2226410Notes

Reaction equation

HRID 2226410 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:19][CH:18]([OH:20])[CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:19][C:18](=[O:20])[CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67788598HCID 67788598, compoundHCID 131709961Jones' reagent

Product 1

HCID 186547871-(Phenylmethyl) (2S)-5-oxo-1,2-piperidinedicarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolve 1 -benzyloxycarbonyl-5-hydroxy-(S)-pipecolic acid (prepared from 5-hydroxy-(S)-pipecolic acid in 2N sodium hydroxide solution treated with benzylchlorformate in diethyl ether) in acetone and treat with Jones reagent to obtain 1-benzyloxycarbonyl-5-keto-(S)-pipecolic acid. Then esterify in methanol to give the respective methyl ester.

Sources & evidence

ORD record
ord-46399973e14c46f0bffeea9d39f41558
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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