3beta-Benzyloxy-5-androsten-17-one → 3beta-Methyl-5alpha-androstan-17-one

HRID 2393209ノート

反応式

HRID 2393209 の反応式
O([C@:3]12[CH2:20][C@@H:19](O)[CH2:18][CH2:17][C@:16]1([CH3:22])[C@@H:15]1[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]1)([CH3:12])[C:10](=[O:23])[CH2:9][CH2:8]3)[CH:5]=[CH:4]2)O.[CH2:24](O[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC2=O)C1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[CH3:24][C@H:19]1[CH2:18][CH2:17][C@@:16]2([CH3:22])[C@@H:3]([CH2:4][CH2:5][C@@H:6]3[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]3[CH2:8][CH2:9][C:10]2=[O:23])[CH2:20]1

参加物

6

反応物 3

HCID 537649083beta-Benzyloxy-5-androsten-17-one2 回HCID 566283895alpha-Hydroperoxy-3beta-hydroxyandrost-6-en-17oneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 186376273beta-Methyl-5alpha-androstan-17-one収率 80%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

実験手順

Firstly an example of catalytic hydrogenation for the synthesis of 5α-androstanes from androst-5-enes is the synthesis of 3β-methyl-5α-androstan-17-one 2 from 3β-methylandrost-5-en-17-one 1. 3β-Methylandrost-5-en-17-one 1 (400 mg), prepared as described previously was dissolved in glacial acetic acid (80 ml). Palladium on carbon (10%, 100 mg) was added and the solution maintained under an atmosphere of hydrogen. When hydrogen uptake ceased, the solution was filtered through celite and evaporated to give solid which was recrystallized from methanol to yield 3β-methyl-5α-androstan-17-one, 2, (320 mg, 80% yield). MP 107°-108° C., 1H NMR (CDCl3) δ0.86 (d, 3H, J-5Hz, methyl at C-3), 0.85 (s, 3H, C-19 Me), 0.79 (s, 3H, C-18 Me).

後処理

  1. temperaturethe solution maintained under an atmosphere of hydrogen
  2. filtrationthe solution was filtered through celite
  3. customevaporated
  4. customto give solid which
  5. customwas recrystallized from methanol

出典と根拠

ORDレコード
ord-9e37747326c444798f22a97ae83dcb7e
出典データセット
uspto-grants-1998_09
特許番号
US05804576

反応ノート

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