tert-Butyl 4-formylpiperidine-1-carboxylate → HCID 178459309, compound

HRID 1620539Notes

Reaction equation

HRID 1620539 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=O.[OH:16][C:17]([CH3:27])([CH3:26])[CH2:18][NH:19][C:20]1[CH2:24][S:23][C:22](=[O:25])[N:21]=1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[OH:16][C:17]([CH3:27])([CH3:26])[CH2:18][NH:19][C:20]1=[N:21][C:22](=[O:25])[S:23]/[C:24]/1=[CH:1]\[CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 3014295Piperidinium acetateHCID 178459301HCID 178459301, compound

Product 1

HCID 178459309HCID 178459309, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 4-formylpiperidine-1-carboxylate (1.70 g) in 2-propanol (30 mL) were added 4-[(2-hydroxy-2-methylpropyl)amino]-1,3-thiazol-2(5H)-one (3.00 g), and piperidinium acetate (1.18 g). The reaction mixture was stirred at 60° C. overnight and concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (1.72 g).

Workup

  1. concentrationconcentrated
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  8. customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-ee73697c73c648b79eb019390daf09cb
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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