Hydrochloric Acid → 3beta-Acetoxy-5alpha-pregnan-20-one

HRID 1529847

Reaktionsgleichung

Reaktionsgleichung von HRID 1529847
[CH3:1][C:2]([C@@H:4]1[C@@:8]2([CH3:23])[CH2:9][CH2:10][C@@H:11]3[C@@:16]4([CH3:22])[CH2:17][CH2:18][C@H:19]([OH:21])[CH2:20][C@@H:15]4[CH2:14][CH2:13][C@H:12]3[C@@H:7]2[CH2:6][CH2:5]1)=[O:3].[C:24](OC(=O)C)(=[O:26])[CH3:25].Cl>N1C=CC=CC=1.C(OCC)C>[C:24]([O:21][C@H:19]1[CH2:18][CH2:17][C@@:16]2([CH3:22])[C@@H:15]([CH2:14][CH2:13][C@@H:12]3[C@@H:11]2[CH2:10][CH2:9][C@@:8]2([CH3:23])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:2](=[O:3])[CH3:1])[CH2:20]1)(=[O:26])[CH3:25]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 92787Isopregnanolone

Produkt 1

HCID 2271133beta-Acetoxy-5alpha-pregnan-20-oneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a stirred suspension of 5α-pregnan-3β-ol-20-one (110) (200 g; 0.628 mol) in pyridine (1750 mL) was added acetic anhydride (593 mL; 6.28 mol). Solid was dissolved after 2 hours and the reaction was left for overnight at room temperature. The reaction mixture was diluted with diethyl ether (5 L) and transferred into a 12 L separatory funnel. The mixture was stirred, while 10% HCl (150 mL) was added by careful monitoring of temperature (maximum temp 35° C.) by an ice bath. The organic layer was washed with ice cold 10% HCl (8×500 mL), with saturated NaHCO3, dried (MgSO4) and concentrated under reduced pressure. The pale yellow solid was dried at 40° C. overnight to give the 3-acetylated compound 111 (223 g; 99%). 1H NMR (300 MHz, CDCl3) δ: 0.58(s, 3H), 0.81(s, 3H), 2.01(s, 3H), 2.10(s, 3H), 2.51(t, 1H, J=9 Hz), 4.67(sept, 1H, J=5 Hz).

Aufarbeitung

  1. dissolutionSolid was dissolved after 2 hours
  2. customtransferred into a 12 L separatory funnel
  3. additionwas added by careful monitoring of temperature (maximum temp 35° C.) by an ice bath
  4. washThe organic layer was washed with ice cold 10% HCl (8×500 mL), with saturated NaHCO3
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe pale yellow solid was dried at 40° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-f284f044aee6404eb8851506622d5df7
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090651B2

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