Methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate → 4-(1-(tert-Butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoic acid

HRID 8746

Reaction equation

HRID 8746 reaction equation
[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][C:6]1([C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.CC(C)=[O:25].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:15]([O:14][C:12]([N:9]1[CH2:8][CH2:7][C:6]([CH2:5][CH2:4][CH2:3][C:2]([OH:25])=[O:1])([C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10]1)=[O:13])([CH3:17])([CH3:18])[CH3:16]

Participants

4

Reactant 2

HCID 86597419Methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylateHCID 131709961Jones' reagent

Product 1

HCID 219839874-(1-(tert-Butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate (23.0 g, 0.0734 mol) from Step C in acetone (775 mL) at room temperature was added Jones reagent (28.2 mL, 2.6M) via syringe. After 5 min, the reaction mixture was concentrated. The residue was taken up in water and diethyl ether and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound (23.4 g) which was used in the next step without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractiondiethyl ether and extracted three times with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-190dcd50c65c412eb9c6458f3623a7b2
Source dataset
uspto-grants-2006_08
Patent number
US07091211B2

Linked notes

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