Sodium cyanoborohydride → HCID 53852576, 화합물

HRID 618871노트

반응식

HRID 618871 반응식
[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]

참가 물질

6

반응물 2

HCID 5003444Sodium cyanoborohydrideHCID 53974580HCID 53974580, 화합물

생성물 1

HCID 53852576HCID 53852576, 화합물수율 74%

시약·촉매·용매 3

HCID 9883512zinc(II)iodide촉매HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4ed2d6d6bdf045a1932235828eaa1923
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05955632

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