Acetic Acid → 3beta-[N-(2-AMINOETHYL)-AMINO]-17beta-HYDROXY-5alpha-ANDROSTANE

HRID 375673

반응식

HRID 375673 반응식
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([CH2:12][C:13](=O)[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[CH2:22]([NH2:25])[CH2:23][NH2:24].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[NH2:24][CH2:23][CH2:22][NH:25][C@H:13]1[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[CH2:19][CH2:20][C@@:3]2([CH3:4])[C@H:5]3[CH2:6][CH2:7][C@@H:2]2[OH:1])[CH2:12]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 3301EthylenediamineHCID 10635DihydrotestosteroneHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 153088353beta-[N-(2-AMINOETHYL)-AMINO]-17beta-HYDROXY-5alpha-ANDROSTANE

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

17β-Hydroxy-5α-androstan-3-one (403 mg, 1.39 mmol)(Aldrich Chemical Company) was added to a stirred solution of 0.745 mL 1,2-ethylenediamine (11.1 mmol) and 1.44 mL acetic acid (25.2 mmol) in 16.0 mL dry methanol (MeOH), followed by 104 mg (1.65 mmol, 1.19 equiv.) of sodium cyanoborohydride. After stirring at room temperature for 15 h, the reaction concentrated under reduced pressure. The residue was partitioned between methylene chloride and aqueous 1N sodium hydroxide, shaken, and separated. The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The product was used without further purification.

후처리

  1. concentrationthe reaction concentrated under reduced pressure
  2. customThe residue was partitioned between methylene chloride and aqueous 1N sodium hydroxide
  3. stirringshaken
  4. customseparated
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product was used without further purification

출처 및 근거

ORD 기록
ord-1c2136c9e3014b3da2cb9b7402937b62
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05486603

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