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

HRID 1357945Notes

Reaction equation

HRID 1357945 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 Ether2×HCID 14798Sodium Hydroxide2×HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1,1-Triacetoxy-1,1-dihydro-1,2-benzoiodoxol-3(1H)-one (750 mg, 1.77 mmol) was added to a solution of 1-(t-butoxycarbonyl)-4-(hydroxymethyl)piperidine (339 mg, 1.57 mmol, from Procedure 17, Step A) in methylene chloride (10 mL) and the mixture was stirred at rt. After 45 min., and additional portion of 1,1,1-triacetoxy-1,1-dihydro-1,2-benzoiodoxol-3(1H)-one (150 mg, 0.35 mmol) was added. After an additional 30 min., ether (30 mL) and 1.3 N NaOH (10 mL) were added and stirring was continued for 20 min. The mixture was transferred to a separatory funnel with additional ether (30 mL) and 1.3 N NaOH (15 mL). The organic layer was separated, washed with water (20 mL), dried (sodium sulfate), decanted, and evaporated to give 291 mg of 1-(t-butoxycarbonyl)-4-piperidinecarboxaldehyde as a colorless oil.

Workup

  1. waitAfter an additional 30 min.
  2. stirringstirring
  3. waitwas continued for 20 min
  4. customThe organic layer was separated
  5. washwashed with water (20 mL)
  6. dry with materialdried (sodium sulfate)
  7. customdecanted
  8. customevaporated

Sources & evidence

ORD record
ord-ba04a20509dd4d9f87cbee0316ff00d5
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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