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

HRID 1858386ノート

反応式

HRID 1858386 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 97%

実験手順

This solution of (S)-azetidine-2-methanol was adjusted to pH 10 by adding 10% sulfuric acid, sodium hydrogen carbonate (2.00 g, 24.0 mmol) was then added, and benzyloxycarbonyl chloride (4.00 g, 24.0 mmol) was added at room temperature. Thereafter, stirring was continued for 14 hours. The reaction mixture was adjusted to pH 7 and extracted with ethyl acetate (50 mL×2), and the extract was washed with water (50 mL×1), dried over magnesium sulfate and filtered. The filtrate was concentrated and 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 (2.14 g, yield 97.0%). The yield was improved as compared with that obtained in Example 1 (69.1%). The formation of the byproduct (S)-2-N-benzyloxycarbonyl-1,4-butanediol decreased to a yield of 2.5% (0.06 g).

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-5d96fe78e27f4f16a80e7b1975705873
出典データセット
uspto-grants-2000_11
特許番号
US06150535

反応ノート

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