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

HRID 891577ノート

反応式

HRID 891577 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-c8504d631a35402fb6e45d55128eeef4
出典データセット
uspto-grants-2006_02
特許番号
US07001897B2

反応ノート

読み込み中…