Diethyl Ether → tert-Butyl 4-formylpiperidine-1-carboxylate

HRID 2185559Notes

Reaction equation

HRID 2185559 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCOCC.[OH-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1,1-Triacetoxy-1,1-dihydro-1,2-benzoiodoxol-3(1H)-one (3.34 g, 7.87 mmol) was added to a solution of 1-(tert-butoxycarbonyl)-4-(hydroxymethyl)piperidine (1.50 g, 6.97 mmol, from Step A) in CH2Cl2 (45 mL) and the mixture was stirred at rt for 40 min. Ether (100 mL) and 1.3 N aq. NaOH (45 mL) were added and stirring was continued for 15 min. After transfer of the mixture to a separatory funnel, the aqueous layer was extracted with ether (50 mL). The organic layers were washed in succession with 1.3 N aq. NaOH (45 mL) and water (50 mL), dried (Mg2SO4), filtered, and evaporated to give 1.21 g of the title compound as a colorless oil.

Workup

  1. stirringstirring
  2. waitwas continued for 15 min
  3. extractionAfter transfer of the mixture to a separatory funnel, the aqueous layer was extracted with ether (50 mL)
  4. washThe organic layers were washed in succession with 1.3 N aq. NaOH (45 mL) and water (50 mL)
  5. dry with materialdried (Mg2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-70b0b5db677d46ca815689f93b9803d1
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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