Ammonium dithiocarbamate → 5-Benzyloxycarbonyl-2-mercapto-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

HRID 440320Notes

Reaction equation

HRID 440320 reaction equation
[C:1](=[S:4])([S-:3])[NH2:2].[NH4+].[CH2:6]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19](=O)[CH:18](Br)[CH2:17]1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C.C(OCC)(=O)C>[CH2:6]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19]2[N:2]=[C:1]([SH:3])[S:4][C:18]=2[CH2:17]1)=[O:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 11083854Ammonium dithiocarbamateHCID 224070023-Bromo-4-oxo-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 1785251075-Benzyloxycarbonyl-2-mercapto-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridineYield 26.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ammonium dithiocarbamate (0.19 g, 1.7 mmol) in 2 mL of ethanol was added 1-benzyloxycarbonyl-3-bromo-4-piperidone (0.53 g, 1.7 mol). The reaction was stirred at rt overnight. The next morning the reaction was heated at 75° C. for 2 h. The reaction was diluted with ethyl acetate and washed with saturated sodium bicarbonate, water (2X) and then brine. The solvent was removed under reduced pressure and the product subjected to flash chromatography (2:1 hexane/ethyl acetate). Crystallization from ethyl acetate/hexane afforded 0.14 g of 5-benzyloxycarbonyl-2-mercapto-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine.

Workup

  1. temperatureThe next morning the reaction was heated at 75° C. for 2 h
  2. washwashed with saturated sodium bicarbonate, water (2X)
  3. customThe solvent was removed under reduced pressure
  4. customCrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-89c4408bb2d34969979bb25306bd98d7
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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