Diethyl Ether → HCID 54416755, compound

HRID 847565Notes

Reaction equation

HRID 847565 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C@@H:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])=[O:9])[CH2:3]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[O-][Si]([O-])=O.[Mg+2].C(OCC)C>C(Cl)Cl>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C@@H:11]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])=[O:9])[CH2:3]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 61680MAGNESIUM SILICATE (synthetic)HCID 2724130Cornforth reagentHCID 18638963HCID 18638963, compound

Product 1

HCID 54416755HCID 54416755, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzyl 2(S)-(3-hydroxypiperidinocarbonyloxy)-3-phenylpropionate (477 mg) in methylene chloride (10 ml) was added pyridinium dichromate (0.99 g) and the mixture was stirred at ambient temperature overnight. The mixture was passed through a Florisil (Trademark : manufactured by Floridin Co.) (60-100 mesh) column with diethyl ether and then methylene chloride as eluent. Concentration under reduced pressure gave benzyl 2(S)-(3-oxopiperidinocarbonyloxy)-3-phenylpropionate (278 mg).

Workup

  1. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-2cc47553ccad4dca8f5fd747166414a9
Source dataset
uspto-grants-1992_08
Patent number
US05142048

Reaction notes

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