Triethylamine → Dihydrotestosterone

HRID 375674

反応式

HRID 375674 の反応式
C(N(CC)CC)C.NCCN[C@H]1C[CH2:28][C@@:27]2([CH3:30])[C@@H:14]([CH2:15][CH2:16][C@@H:17]3[C@@H:26]2[CH2:25][CH2:24][C@@:22]2([CH3:23])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[OH:31])[CH2:13]1.FC(F)(F)C([O:36][CH2:37][CH3:38])=O>CO>[OH:31][C@H:21]1[CH2:20][CH2:19][C@H:18]2[C@H:17]3[C@H:26]([CH2:25][CH2:24][C@:22]12[CH3:23])[C@:27]1([CH3:28])[C@H:14]([CH2:13][C:37](=[O:36])[CH2:38][CH2:30]1)[CH2:15][CH2:16]3

参加物

5

反応物 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 153088353beta-[N-(2-AMINOETHYL)-AMINO]-17beta-HYDROXY-5alpha-ANDROSTANE

生成物 1

HCID 10635Dihydrotestosterone収率 21.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Triethylamine (TEA) (3.0 mL, 21.5 mmol, 15.5 equiv.) was added to 1.39 mmol of crude 3β-[N-(2-aminoethyl)-amino]-17β-hydroxy-5α-androstane in 8.0 mL dry methanol, followed by 3.21 mL (27.0 mmol, 19.4 equiv.) of ethyl trifluoroacetate (Aldrich). After stirring for 22 h at room temperature, the reaction was concentrated on a rotary evaporator. The residue was partitioned between methylene chloride and aqueous 1N hydrogen chloride (HCl), shaken, and separated. The organic layer was washed with water, saturated aqueous sodium bicarbonate, water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography on a 20 mm column using one column volume of methylene chloride, one column volume of 5% methanol in methylene chloride, and then one column volume of 10% methanol in methylene chloride, as eluants. Isolation and concentration of the product afforded 155 mg (21.2% yield over two steps from 17β-hydroxy-5α-androstan-3-one) of pure product.

後処理

  1. concentrationthe reaction was concentrated on a rotary evaporator
  2. customThe residue was partitioned between methylene chloride and aqueous 1N hydrogen chloride (HCl)
  3. stirringshaken
  4. customseparated
  5. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate, water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product was purified by flash chromatography on a 20 mm column

出典と根拠

ORDレコード
ord-6c976da15c804e9dbaa8d8742e839e47
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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