Trifluoroacetic anhydride → Isopregnanolone

HRID 375672

反応式

HRID 375672 の反応式
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].N[CH:15]([C@@H:17]1[C@:34]2([CH3:35])[C@H:20]([C@H:21]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C@H:24]([CH2:25][C@@H:26]([OH:36])[CH2:27][CH2:28]2)[CH2:23][CH2:22]3)[CH2:19][CH2:18]1)[CH3:16]>N1C=CC=CC=1>[OH:36][C@H:26]1[CH2:27][CH2:28][C@@:29]2([CH3:30])[C@@H:24]([CH2:23][CH2:22][C@@H:21]3[C@@H:31]2[CH2:32][CH2:33][C@@:34]2([CH3:35])[C@H:20]3[CH2:19][CH2:18][C@@H:17]2[C:15](=[O:4])[CH3:16])[CH2:25]1

参加物

4

反応物 2

HCID 9845Trifluoroacetic anhydrideHCID 1031390020-Amino-3beta-hydroxy-5alpha-pregnane

生成物 1

HCID 92787Isopregnanolone収率 52.9%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

20-Amino-3β-hydroxy-5α-pregnane was first concentrated from dry pyridine. Trifluoroacetic anhydride (3.0 mL) was then carefully added to 3.04 mmol of crude 20-amino-3β-hydroxy-5α-pregnane resuspended in 5.0 mL dry pyridine. After stirring the reaction mixture at room temperature for 3.5 h, the reaction mixture was partitioned between diethyl ether and 1N aqueous HCl, shaken and separated. The organic layer was successively washed with 1N aqueous HCl, water, saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was refluxed in 15.0 mL methanol for 26 h and then concentrated. The residue was purified by flash chromatography on a 25 mm column using first one column volume of methylene chloride, then one column volume of 5% ethyl acetate in methylene chloride, and then 10% ethyl acetate in methylene chloride as eluants. Isolation and concentration of the product afforded 668 mg (52.9% yield over three steps, from 3β-hydroxy-5α-pregnan-20-one) of product.

後処理

  1. concentration20-Amino-3β-hydroxy-5α-pregnane was first concentrated from dry pyridine
  2. customthe reaction mixture was partitioned between diethyl ether and 1N aqueous HCl
  3. stirringshaken
  4. customseparated
  5. washThe organic layer was successively washed with 1N aqueous HCl, water, saturated aqueous sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. temperatureThe residue was refluxed in 15.0 mL methanol for 26 h
  10. concentrationconcentrated
  11. customThe residue was purified by flash chromatography on a 25 mm column

出典と根拠

ORDレコード
ord-49140151618844b695e77263d84376e6
出典データセット
uspto-grants-1996_01
特許番号
US05486603

関連ノート

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