Potassium Carbonate → HCID 54424373, compound

HRID 1858707Notes

Reaction equation

HRID 1858707 reaction equation
Br[CH:2]1[C:7](=[O:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[SH:16][CH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[CH2:17][S:16][CH:2]1[C:7](=[O:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53142682-NaphthalenemethanethiolHCID 106839701-tert-Butyloxycarbonyl-3-bromo-4-oxopiperidine

Product 1

HCID 54424373HCID 54424373, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.78 g (10 mmol) of tert-butyl 3-bromo-4-oxo-piperidine-1-carboxylate and 2.09 g (12 mmol) of 2-mercaptomethylnaphthalene in 100 ml of absolute acetonitrile was treated with 13.8 g (100 mmol) of anhydrous potassium carbonate and thereafter the mixture was stirred at room temperature for 18 hours. The reaction mixture was filtered, the filtrate was poured on to ice-water and adjusted to pH 2-3 with concentrated hydrochloric acid; the aqueous phase was extracted three times with 200 ml of ethyl acetate each time, the organic phase was washed once with 200 ml of water, dried over magnesium sulphate, filtered and concentrated in a water-jet vacuum. The crude product (5.5 g) was chromatographed on silica gel with hexane and ethyl acetate as the eluent. The product was recrystallized from ethyl acetate and hexane. There were obtained 2.27 g (61% of theory) of tert-butyl (3RS)-3-(naphthalen-2-ylmethylthio)-4-oxo-piperidine-1-carboxylate as a colourless solid; MS: 371 (M)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was poured on to ice-water
  3. extractionthe aqueous phase was extracted three times with 200 ml of ethyl acetate each time
  4. washthe organic phase was washed once with 200 ml of water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in a water-jet vacuum
  8. customThe crude product (5.5 g) was chromatographed on silica gel with hexane and ethyl acetate as the eluent
  9. customThe product was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-b5e05f174d3e469388f0c2c47e429a95
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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