Chloroform → HCID 57602861, compound

HRID 1788389Notes

Reaction equation

HRID 1788389 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][CH2:15][OH:16])[CH2:10][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])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 22594495tert-Butyl 4-(2-hydroxyethylidene)piperidine-1-carboxylate

Product 1

HCID 57602861HCID 57602861, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8058HexaneSolvent

Procedure

To a solution of 4-(2-hydroxyethylidene)piperidine-1-carboxylic acid t-butyl ester (10.4 g, 46 mmol) in a mixture of hexane (300 mL)-chloroform (100 mL) was added manganese dioxide (100 g), 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 9.2 g (yield 89%) of 4-(2-oxoethylidene)piperidine-1-carboxylic acid t-butyl ester (VII-18, 20, 21, 24, 30, 41, 42, 43, 44, 45).

Workup

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

Sources & evidence

ORD record
ord-837679e5d7ae48f7b6381523e1ee1665
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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