Chloroform → HCID 86595276, compound

HRID 1788394Notes

Reaction equation

HRID 1788394 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][CH2:15][OH:16])[C:10]([CH3:18])([CH3:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)Cl>CCCCCC.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][CH:15]=[O:16])[C:10]([CH3:18])([CH3:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 68824202HCID 68824202, compound

Product 1

HCID 86595276HCID 86595276, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8058HexaneSolvent

Procedure

Manganese dioxide (10 g) was added to a solution of 4-(2-hydroxyethylidene)-3,3-dimethylpiperidine-1-carboxylic acid t-butyl ester (0.9 g, 3.5 mmol) in a mixture of hexane (30 mL)-chloroform (10 mL) and stirred for 10 hours. After the reaction was completed, insoluble materials were filtered off through Celite, and the filtrate was concentrated under a reduced pressure to obtain 0.63 g (yield 70.8%) of 3,3-dimethyl-4-(2-oxoethylidene)piperidine-1-carboxylic acid t-butyl ester (VII-141, 142). Its physical property is shown below.

Workup

  1. filtrationinsoluble materials were filtered off through Celite
  2. concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-be4546298cda49fca703fee5e512e5ba
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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