Sodium hydride → (2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-[(1-thioxopropyl)thio]pyrrolidine

HRID 1464721ノート

反応式

HRID 1464721 の反応式
[H-].[Na+].[C:3]([SH:7])(=[S:6])[CH2:4][CH3:5].[CH2:8]([O:11][C:12]([N:14]1[CH2:18][C@H:17](OS(C)(=O)=O)[CH2:16][C@H:15]1[CH2:24][O:25][CH2:26][CH2:27][F:28])=[O:13])[CH:9]=[CH2:10]>O1CCCC1>[CH2:8]([O:11][C:12]([N:14]1[CH2:18][C@@H:17]([S:6][C:3](=[S:7])[CH2:4][CH3:5])[CH2:16][C@H:15]1[CH2:24][O:25][CH2:26][CH2:27][F:28])=[O:13])[CH:9]=[CH2:10]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 10176109Propanedithioic AcidHCID 57165653(2S,4R)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methylsulfonyloxypyrrolidine

生成物 1

HCID 57310918(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-[(1-thioxopropyl)thio]pyrrolidine収率 60%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of sodium hydride (60% in oil, 2.0 g) in anhydrous tetrahydrofuran (50 ml) was added propanedithioic acid (5.0 g) with ice-cooling. A solution of (2S,4R)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methylsulfonyloxypyrrolidine (16.25 g) in anhydrous tetrahydrofuran (50 ml) was added dropwise to the mixture and the mixture was heated at 60°-70° C. for 4 hours. The solution was poured into ice-water (100 ml) and extracted with diethyl ether. The organic layer was washed with 1N aqueous sodium hydroxide solution (50 ml) and brine, dried, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel [n-hexane-ethyl acetate (10:1, V/V)] to afford (2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-[(1-thioxopropyl)thio]pyrrolidine (9.47 g).

後処理

  1. temperaturecooling
  2. temperaturethe mixture was heated at 60°-70° C. for 4 hours
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with 1N aqueous sodium hydroxide solution (50 ml) and brine
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel [n-hexane-ethyl acetate (10:1, V/V)]

出典と根拠

ORDレコード
ord-7b7619e10011423fa6aec898a94e952e
出典データセット
uspto-grants-1994_04
特許番号
US05306816

反応ノート

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