Pyridine → HCID 57251409、化合物

HRID 257744

反応式

HRID 257744 の反応式
[C:1]([C:3](O)([C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12](=[CH:13][C:14](=[O:24])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH2:6]1)[CH3:4])#[N:2].CC([C@@H]1[C@@]2(C)CC[C@@H]3[C@]4(C)C(=CC(CC4)=O)CC[C@H]3[C@@H]2CC1)=O.CS(Cl)(=O)=O.N1C=CC=CC=1>CC(C)(O)C#N.C(N(CC)CC)C.O>[C:1]([C:3](=[C:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12](=[CH:13][C:14](=[O:24])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH2:6]1)[CH3:4])#[N:2]

参加物

8

反応物 4

HCID 1049PyridineHCID 5994Progesterone3 回HCID 31297Methanesulfonyl chlorideHCID 57016276HCID 57016276、化合物

生成物 1

HCID 57251409HCID 57251409、化合物

試薬・触媒・溶媒 3

HCID 8471Triethylamine触媒HCID 962Water溶媒HCID 6406Acetone Cyanohydrin溶媒

実験手順

The procedure of Ercoli and Ruggieri (Gazz. Chim. Ital. 84, 312, 1954, incorporated herein by reference) was followed to prepare 20-cyano-20-hydroxy-4-pregnene-3-one (I-25) from progesterone. Thus, the suspension of progesterone 1.2 g in acetone cyanohydrin 2.4 ml was stirred and warmed at 40° C. until all the progesterone was dissolved. Four drops of triethylamine was then added. After 2 h the precipitate was filtered and dried to give crude I-25 1.4 g; m.p. 188°-90° C. After recrystallization from ethanol (contained 1% acetic acid), the product was obtained as fine crystals, m.p. 199°-200° C. The mixture containing cyanohydrin (I-25) 0.4 g, methane sulfonyl chloride 1 ml and pyridine 5 ml was stirred at room temperature for 5 h, then at 80° C. for 1 h. Water 20 ml was added and the precipitate was collected. The crude product was chromatographed on silica gel TLC plate (developed by hexane:/ethyl acetate, 1:1). The yield of I-26 was 80 mg, m.p. 195°-6° C.

後処理

  1. dissolutionwas dissolved
  2. filtrationAfter 2 h the precipitate was filtered
  3. customdried
  4. customto give crude I-25 1.4 g
  5. customAfter recrystallization from ethanol (contained 1% acetic acid)
  6. customthe product was obtained as fine crystals, m.p. 199°-200° C
  7. stirringwas stirred at room temperature for 5 h
  8. customthe precipitate was collected
  9. customThe crude product was chromatographed on silica gel TLC plate (developed by hexane:/ethyl acetate, 1:1)

出典と根拠

ORDレコード
ord-a5d6303b872740528978fc0fbdf3919b
出典データセット
uspto-grants-1993_11
特許番号
US05264427

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