HCID 22258851, compound → tert-butyl 5-formyl-3,6-dihydro-1(2H)-pyridinecarboxylate

HRID 1767338Notes

Reaction equation

HRID 1767338 reaction equation
[OH:1][CH2:2][C:3]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][CH:4]=1>ClCCl.O=[Mn]=O>[CH:2]([C:3]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][CH:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 22258851HCID 22258851, compound

Product 1

HCID 22258875tert-butyl 5-formyl-3,6-dihydro-1(2H)-pyridinecarboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-(hydroxymethyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (14.65 g, 68.69 mmol) in dichloromethane was added MnO2 (89.58 g, 1030.36 mmol), then stirred overnight at room temperature. The reaction mixture was filtered through Celite®, the filtrate was concentrated under reduced pressure to give tert-butyl 5-formyl-3,6-dihydro-1(2H)-pyridinecarboxylate, which was pure enough to be used for the next reaction. (13.55 g, yield 94%)

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a060df648fa944208047d9bed82f1db8
Source dataset
uspto-grants-2007_06
Patent number
US07232909B2

Reaction notes

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