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1,4-Dioxane → (2S,4S)-N-methanesulfonyl-2-tert-butyldimethylsilyloxymethyl-4-diphenylphosphinopyrrolidine

HRID 1638406
ノート
印刷プレビュー

反応式

HRID 1638406 の反応式
O1CCOCC1.Cl[P:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Na].[CH3:22][S:23]([N:26]1[CH2:30][C@H:29](OS(C)(=O)=O)[CH2:28][C@H:27]1[CH2:36][O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])(=[O:25])=[O:24]>O1CCCC1>[CH3:22][S:23]([N:26]1[CH2:30][C@@H:29]([P:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:28][C@H:27]1[CH2:36][O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:39])[CH3:40])(=[O:24])=[O:25]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 312751,4-DioxaneHCID 66180ChlorodiphenylphosphineHCID 5360545SodiumHCID 13665135(2S,4R)-N-methanesulfonyl-2-tert-butyldimethylsilyloxymethyl-4-methanesulfonyloxypyrrolidine

生成物 1

HCID 13665138(2S,4S)-N-methanesulfonyl-2-tert-butyldimethylsilyloxymethyl-4-diphenylphosphinopyrrolidine収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To 150 ml of dioxane were added 11.39 g (0.052 mol) of chlorodiphenylphosphine and 2.6 g (0.114 mol) of sodium, and the mixture was refluxed for 4 hours in nitrogen atmosphere. After allowing the mixture to stand for cooling, 50 ml of tetrahydrofuran was added to the reaction mixture, and a solution of 10.45 g (0.027 mol) of (2S,4R)-N-methanesulfonyl-2-tert-butyldimethylsilyloxymethyl-4-methanesulfonyloxypyrrolidine [V] in 100 ml of tetrahydrofuran was added dropwise to the mixture lest any air should enter in the reaction system. The mixture was stirred in nitrogen atmosphere at 0° C. for 2 hours and then at room temperature overnight and then any insoluble matter was removed, for example, by filtration. The filtrate was concentrated until dryness under reduced pressure and the residue was purified by column chromatography on silica gel whereby 7.93 g (yield: 62%) of an oily substance was obtained.

後処理

  1. temperaturethe mixture was refluxed for 4 hours in nitrogen atmosphere
  2. temperaturefor cooling
  3. customat room temperature
  4. customovernight
  5. concentrationThe filtrate was concentrated until dryness under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel whereby 7.93 g (yield: 62%) of an oily substance
  7. customwas obtained

出典と根拠

ORDレコード
ord-2f511b833e9a47b0bd8bdd3795062de1
出典データセット
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04879389

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート