Hydrochloric Acid → 21-Chloromethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1973735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1973735
[OH:1][C@@H:2]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:19]2[C:18](=[O:24])[CH2:17][C@@:16]2([CH3:25])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:15])[CH:13]=[CH2:14])[CH2:3]1.[ClH:26].O>O1CCOCC1>[Cl:26][CH2:14][CH2:13][C:12](=[O:15])[C@@H:11]1[C@:16]2([CH3:25])[C@H:8]([C@H:7]3[C@H:19]([C:18](=[O:24])[CH2:17]2)[C@:20]2([CH3:23])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:22][CH2:21]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86734286HCID 86734286, Verbindung

Produkt 1

HCID 8673430721-Chloromethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

3α-Hydroxy-21-methylene-5α-pregnane-11,20-dione (500 mg) was dissolved in dioxan (40 ml) and dry hydrogen chloride passed through the solution for 1 hour. The mixture was left to stand for a further 2 hours, then poured into water and the sticky solid extracted into ether. The extracts were washed with saturated sodium bicarbonate, water and then dried over anhydrous sodium sulphate. After evaporation and trituration of the resulting foam with ether/petrol the title compound (375 mg) was obtained as a white solid. m.p. 110°-112° with gas evolution [α]D + 100° (c = 1.06).

Aufarbeitung

  1. waitThe mixture was left
  2. extractionthe sticky solid extracted into ether
  3. washThe extracts were washed with saturated sodium bicarbonate, water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customAfter evaporation and trituration of the resulting foam with ether/petrol the title compound (375 mg)
  6. customwas obtained as a white solid
  7. custom100° (c = 1.06)

Quellen und Nachweise

ORD-Eintrag
ord-80e6cf0b5f6b4509a8f02115f79cdaf6
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03998829

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