Triethylamine → Dihydrotestosterone

HRID 375674

반응식

HRID 375674 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 10635Dihydrotestosterone수율 21.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6c976da15c804e9dbaa8d8742e839e47
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05486603

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