Diethyl Ether → Benzyl 4-formylpiperidine-1-carboxylate

HRID 1357906Notes

Reaction equation

HRID 1357906 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][OH:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOCC.[OH-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 14798Sodium Hydroxide2×HCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 2776272Benzyl 4-formylpiperidine-1-carboxylateYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1,1-Triacetoxy-1,1-dihydro-1,2-benzoiodoxol-3(1H)-one (1.92 g, 4.53 mmol) was added to a solution of 1-(benzyloxycarbonyl)-4-(hydroxymethyl)piperidine (1.00 g, 4.01 mmol) in methylene chloride (20 mL) and the mixture was stirred at rt for 45 min. Ether (75 mL) and 1.3 N aq. NaOH (25 mL) were added and stirring was continued for 15 min. The mixture was transferred to a separatory funnel with additional ether (30 mL) and 1.3 N aq. NaOH (20 mL). The organic layer was separated, washed with saturated aq. brine (20 mL), dried (sodium sulfate), decanted, and evaporated to give 846 mg of 1-(benzyloxycarbonyl)4-piperidine carboxaldehyde as a colorless syrup.

Workup

  1. stirringstirring
  2. waitwas continued for 15 min
  3. customThe organic layer was separated
  4. washwashed with saturated aq. brine (20 mL)
  5. dry with materialdried (sodium sulfate)
  6. customdecanted
  7. customevaporated

Sources & evidence

ORD record
ord-b7f903328e3d452d93b4f4f998a4bb8b
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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