Sulfuric Acid → (S)-2-Hydroxymethyl-azetidine-1-carboxylic acid benzyl ester

HRID 1858389ノート

反応式

HRID 1858389 の反応式
[NH:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][OH:6].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].[CH2:17]([O:24][C:25](Cl)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([O:24][C:25]([N:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][OH:6])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 4

HCID 1118Sulfuric AcidHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 10855374(S)-Azetidin-2-ylmethanol

生成物 1

HCID 10900173(S)-2-Hydroxymethyl-azetidine-1-carboxylic acid benzyl ester収率 75%

実験手順

Said solution of (S)-azetidine-2-methanol was adjusted to pH 10 by adding 10% sulfuric acid, sodium hydrogen carbonate (0.88 g, 10.5 mmol) was then added, and benzyloxycarbonyl chloride (1.76 g, 10.3 mmol) was added thereto at room temperature, followed by 14 hours of stirring. The solution was adjusted to pH 7 and extracted with ethyl acetate (50 mL ×2), the extract was washed with water (50 mL×1), dried over magnesium sulfate and filtered, and the filtrate was concentrated. The concentrate was subjected to column chromatography (Wakogel C-200) using toluene/ethyl acetate (1/1) as a mobile phase for separation/purification, to give (S)-N-benzyloxycarbonylazetidine-2-methanol (0.781 g, yield 75%) as a pale yellow oil. (S)-2-N-benzyloxycarbonyl-1,4-butanediol was obtained as a byproduct (0.096 g, yield 9%).

後処理

  1. additionwas then added
  2. extractionextracted with ethyl acetate (50 mL ×2)
  3. washthe extract was washed with water (50 mL×1)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customfor separation/purification

出典と根拠

ORDレコード
ord-6d64ae7e557f4d218f13d91dd013be6a
出典データセット
uspto-grants-2000_11
特許番号
US06150535

反応ノート

読み込み中…