HCID 59803202, compound → HCID 59803209, compound

HRID 1801592Notes

Reaction equation

HRID 1801592 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11]1>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11]1

Participants

4

Reactant 1

HCID 59803202HCID 59803202, compound

Product 1

HCID 59803209HCID 59803209, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 1-(2-chloro-5-(hydroxymethyl)phenyl)piperidine-4-carboxylate 67 (0.198 g, 0.698 mmol) in DCM (3.5 mL) was added MnO2 (0.688 mg, 7.91 mmol). The reaction mixture was stirred at room temperature for 17 h, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 10% to 40% EtOAc in hexanes) gave methyl 1-(2-chloro-5-formylphenyl)piperidine-4-carboxylate 68 (0.150 g, 76.3% yield) as a colorless oil. Mass spectrum: calculated for C14H16ClNO3 281.1. found 282.1 (M++1).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customPurification by flash column chromatography on silica gel (eluted with 10% to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a3ed95b4635d459681e25f7b7d1f0c99
Source dataset
uspto-grants-2013_01
Patent number
US08349831B2

Reaction notes

Loading…