Potassium bisulfate → tert-Butyl 4-formylpiperidine-1-carboxylate

HRID 1063368Notes

Reaction equation

HRID 1063368 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20](=[O:25])N(OC)C)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].OS([O-])(=O)=O.[K+]>C1COCC1>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([CH:20]=[O:25])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateYield 108%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.46 g (143.8 mmol) of LAH in 600 ml THF was cooled (−50° C.) and treated during 25 min with a solution of 35.6 g (130.7 mmol) of 4-(Methoxy-methyl-carbamoyl)-piperidine-1-carboxylic acid tert-butyl ester in 600 ml THF. The reaction was warmed up to RT for 3.5 h, cooled (−78° C.) and hydrolyzed with a suspension of 35 g MgSO4.7H2O, 35 g silicagel in 130 ml aqueous 10% KHSO4. The cooling bath was removed, THF was added, the mixture was stirred for 30 min and filtered. After evaporation, the residue was dissolved in CH2Cl2, dried (Na2SO4) and evaporated to give 30.1 g (quantitative) of 4-Formyl-piperidine-1-carboxylic acid tert-butyl ester, MS: 213 (M).

Workup

  1. temperaturecooled (−78° C.)
  2. customThe cooling bath was removed
  3. additionTHF was added
  4. filtrationfiltered
  5. customAfter evaporation
  6. dissolutionthe residue was dissolved in CH2Cl2
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-f4fd6cf886844fe1ba60134930b60649
Source dataset
uspto-grants-2005_11
Patent number
US06964974B2

Reaction notes

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