Sodium cyanoborohydride → HCID 53852576、化合物

HRID 618871ノート

反応式

HRID 618871 の反応式
[C:1]([O:4][C@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[CH:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C:11]3=[CH:12][CH2:13][C@@H:14]2[C:15](=O)[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].C([BH3-])#N.[Na+]>CC(O)=O.CO.[I-].[Zn+2].[I-]>[C:1]([O:4][C@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[CH:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C:11]3=[CH:12][CH2:13][C@@H:14]2[CH2:15][CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

参加物

6

反応物 2

HCID 5003444Sodium cyanoborohydrideHCID 53974580HCID 53974580、化合物

生成物 1

HCID 53852576HCID 53852576、化合物収率 74%

試薬・触媒・溶媒 3

HCID 9883512zinc(II)iodide触媒HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

A solution of 5.2 g of 3β-acetoxy-pregn-14-en-20-one (Gambara, T. et al, Chem. Pharm. Bull., 1970, 18, 453) and p-toluensulphonyl hydrazide (3.5 g) in AcOH (50 mL) was stirred at room temp. for 3 hrs. The solvent was evaporated to dryness under reduced pressure: the residue obtained was dissolved in MeOH (200 mL) and zinc iodide (0.6 g) was added. To this solution sodium cyanoborohydride (1.5 g) was added portionwise and the temperature was raised to the boiling point of the reaction mixture. After 2 hrs the solvent was evaporated to dryness under reduced pressure, the crude product was dissolved in ethyl acetate and neutralised with 0.1 N NaOH; the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 97/3 as eluant to give 3.7 g of 3β-acetoxy-pregn-14-ene as a white solid.

後処理

  1. customThe solvent was evaporated to dryness under reduced pressure
  2. customthe residue obtained
  3. temperaturethe temperature was raised to the boiling point of the reaction mixture
  4. customAfter 2 hrs the solvent was evaporated to dryness under reduced pressure
  5. dissolutionthe crude product was dissolved in ethyl acetate and neutralised with 0.1 N NaOH
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was purified by flash-chromatography (SiO2)

出典と根拠

ORDレコード
ord-4ed2d6d6bdf045a1932235828eaa1923
出典データセット
uspto-grants-1999_09
特許番号
US05955632

反応ノート

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