Diethyl Ether → Benzyl 4-formylpiperidine-1-carboxylate

HRID 1386765Notes

Reaction equation

HRID 1386765 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 CH2Cl2 (20 mL) and the mixture was stirred at RT for 45 min. Ether (75 mL) and 1.3 N 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 NaOH (20 mL). The organic layer was separated, washed with saturated aq. NaCl (20 mL, dried (Na2SO4), 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. NaCl (20 mL
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-4101925129fa40d5a9be27c28aac380e
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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