Ethyl isothiocyanatoformate → [(3R)-3-hydroxypyrrolidine-1-carbothioyl]carbamic acid ethyl ester

HRID 891577Notes

Reaction equation

HRID 891577 reaction equation
Cl.[OH:2][C@@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[CH2:8]([O:10][C:11]([N:13]=[C:14]=[S:15])=[O:12])[CH3:9]>O1CCCC1>[CH2:8]([O:10][C:11](=[O:12])[NH:13][C:14]([N:5]1[CH2:6][CH2:7][C@@H:3]([OH:2])[CH2:4]1)=[S:15])[CH3:9]

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 2759336(3R)-pyrrolidin-3-ol hydrochloride

Product 1

HCID 86590852[(3R)-3-hydroxypyrrolidine-1-carbothioyl]carbamic acid ethyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3R)-3-hydroxypyrrolidine hydrochloride (15 g, 121.4 mmol) was dissolved in tetrahydrofuran (450 ml), and ethoxycarbonyl isothiocyanate (15.7 ml) was added thereto in an ice bath. The mixture solution was brought to room temperature in 10 minutes and then stirred overnight. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from a mixture of ethyl acetate and n-hexane to afford [(3R)-3-hydroxypyrrolidine-1-carbothioyl]carbamic acid ethyl ester (24.62 g, yield 93%) as a yellow crystal.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-c8504d631a35402fb6e45d55128eeef4
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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