4-(1-Phenyl-1-(3-hydroxy-1-butyn-1-yl)-methylene)-piperidine-1-carboxylic Acid Tert-Butyl Ester → 4-(1-Phenyl-1-(3-oxo-1-butyn-1-yl)methylene)-piperidine-1-carboxylic Acid Tert-Butyl Ester

HRID 606770Notes

Reaction equation

HRID 606770 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]#[C:16][CH:17]([OH:19])[CH3:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[C:14]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:15]#[C:16][C:17](=[O:19])[CH3:18])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 866219574-(1-Phenyl-1-(3-hydroxy-1-butyn-1-yl)-methylene)-piperidine-1-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 865943864-(1-Phenyl-1-(3-oxo-1-butyn-1-yl)methylene)-piperidine-1-carboxylic Acid Tert-Butyl EsterYield 97%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-phenyl-1-(3-hydroxy-1-butyn-1-yl)-methylene)-piperidine-1-carboxylic acid tert-butyl ester (0.197 g, 0.577 mmol) in CH2Cl2 (5 mL) was added activated MnO2 (1.125 g) at 0° C. The mixture was allowed to stir for 3 h, at which point no starting material remained. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated to give the title compound (0.190 g, 97%) as a colorless oil:

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d0f362a9dbc84f219d666c0b3487b8cc
Source dataset
uspto-grants-2011_03
Patent number
US07915283B2

Reaction notes

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