HCID 22032377, compound → HCID 22031666, compound

HRID 1792498Notes

Reaction equation

HRID 1792498 reaction equation
[OH:1][CH:2]([C:16]1[S:17][C:18]([S:21][CH3:22])=[CH:19][CH:20]=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>CC(C)=O.[O-2].[O-2].[Mn+4]>[CH3:22][S:21][C:18]1[S:17][C:16]([C:2]([CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)=[O:1])=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 22032377HCID 22032377, compound

Product 1

HCID 22031666HCID 22031666, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

1.41 g of t-butyl 4-[hydroxy-(5-methylsulfanylthiophen-2-yl)-methyl]-piperidine-1-carboxylate (compound in Production Example 389) was dissolved in 40 mL acetone, and 14 g manganese dioxide was added thereto and stirred at room temperature for 24 hours. The reaction mixture was filtered through Celite, then the solvent was removed to give 1.14 g t-butyl 4-(5-methylsulfanylthiophen-2-carbonyl)piperidine-1-carboxylate, 5 mL of 4 N hydrogen chloride in ethyl acetate was added thereto, and the mixture was left for 1 hour. The solvent was removed, and the precipitated crystals were washed with ethyl acetate/ether, to give 0.75 g of the title compound as colorless crystals.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-d751c0626a6448e78cef8dabd2d464de
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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