1,2-Dichloroethane → 17-Hydroxyprogesterone

HRID 433655

Reaktionsgleichung

Reaktionsgleichung von HRID 433655
[CH3:1][C:2]([C:4]1[C@@:8]2([CH3:23])[CH2:9][CH2:10][C@@H:11]3[C@:21]4([CH3:22])[C:15](=[CH:16][C:17]([CH2:19][CH2:20]4)=[O:18])[CH2:14][CH2:13][C@H:12]3[C@@H:7]2[CH2:6][CH:5]=1)=[O:3].ClCCCl.C([OH:31])(C)C>>[CH3:1][C:2]([C@:4]1([OH:31])[C@@:8]2([CH3:23])[CH2:9][CH2:10][C@@H:11]3[C@:21]4([CH3:22])[C:15](=[CH:16][C:17]([CH2:19][CH2:20]4)=[O:18])[CH2:14][CH2:13][C@H:12]3[C@@H:7]2[CH2:6][CH2:5]1)=[O:3]

Komponenten

4

Edukt 3

HCID 111,2-DichloroethaneHCID 3776IsopropanolHCID 101964Pregna-4,16-diene-3,20-dione

Produkt 1

HCID 623817-HydroxyprogesteroneAusbeute 85 %

Versuchsvorschrift

To a stirred solution of 16-dehydroprogesterone 3 (0.041 g, 0.131 mmol, 1.0 equ) and Mn(dpm)3 (0.002 g, 0.003 mmol, 0.02 eq) in a mixture of isopropanol (1.5 mL) and enough 1,2-dichloroethane (0.6 mL) to completely dissolve the starting material at 0° C. for 20 min. then at room temperature for 2 h under O2. The solvents were removed by distillation under reduced pressure, affording a cream solid. Purification by flash column chromatography over silica, eluting with 30% EtOAc-hexanes afforded the 17 α-hydroxyprogesterone 4 as a white crystalline solid (0.037 g, 85%) which was identical in all respects with an authentic sample.

Aufarbeitung

  1. dissolutionto completely dissolve the starting material at 0° C. for 20 min.
  2. customThe solvents were removed by distillation under reduced pressure
  3. customaffording a cream solid
  4. customPurification by flash column chromatography over silica
  5. washeluting with 30% EtOAc-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-359fa1ad251047b6b2c0b81009c88da8
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06667410B2

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