Water → (2S,4R)-N-methanesulfonyl-4-hydroxy-2-hydroxymethylpyrrolidine

HRID 1638404ノート

反応式

HRID 1638404 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C@@H:11]1[CH2:15][C@@H:14]([OH:16])[CH2:13][N:12]1[S:17]([CH3:20])(=[O:19])=[O:18])C.O>O1CCCC1>[CH3:20][S:17]([N:12]1[CH2:13][C@H:14]([OH:16])[CH2:15][C@H:11]1[CH2:10][OH:9])(=[O:19])=[O:18]

参加物

5

反応物 3

HCID 962WaterHCID 13665129(2S,4R)-N-methanesulfonyl-4-hydroxyproline ethyl esterHCID 21226445Aluminium lithium hydride

生成物 1

HCID 13665131(2S,4R)-N-methanesulfonyl-4-hydroxy-2-hydroxymethylpyrrolidine収率 87%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To 360 ml of tetrahydrofuran was added 3.98 g (0.105 mol) of lithium aluminum hydride, and the mixture was stirred. To this mixture was slowly added dropwise a solution of 16.6 g (0.07 mol) of (2S,4R)-N-methanesulfonyl-4-hydroxyproline ethyl ester [III] in 200 ml of tetrahydrofuran under agitation and ice-cooling. After stirring the suspension at 0° C. for 3 hours and then at room temperature for 3 hours, 14 ml of water was added dropwise in small portions to the suspension under ice-cooling, and thereafter the mixture was stirred for 30 minutes. Any insoluble matter was removed by filtration and the filtrate was concentrated until dryness under reduced pressure whereby 11.9 g (yield: 87%) of an oily substance was obtained.

後処理

  1. temperaturecooling
  2. stirringAfter stirring the suspension at 0° C. for 3 hours
  3. temperaturecooling
  4. stirringthe mixture was stirred for 30 minutes
  5. customAny insoluble matter was removed by filtration
  6. concentrationthe filtrate was concentrated until dryness under reduced pressure whereby 11.9 g (yield: 87%) of an oily substance
  7. customwas obtained

出典と根拠

ORDレコード
ord-65a39665da7e44d1b0825f935b44ec28
出典データセット
uspto-grants-1989_11
特許番号
US04879389

反応ノート

読み込み中…