Imidazole → 3beta-Tert-butyldimethylsilyloxy-17beta-(3-furyl)-5beta-androstan-14beta-ol

HRID 1647642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647642
[O:1]1[CH:5]=[CH:4][C:3]([C@H:6]2[CH2:11][CH2:10][C@:9]3([OH:26])[C@H:12]4[C@H:22]([CH2:23][CH2:24][C@:7]23[CH3:8])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([OH:25])[CH2:18][CH2:19]2)[CH2:14][CH2:13]4)=[CH:2]1.O1[C@@H]2C[C@H](C3C=COC=3)[C@]3(CC[C@H]4[C@H]([C@@]123)CC[C@H]1[C@]4(C)CC[C@H](O)C1)C.N1C=CN=C1.[Si:58](Cl)([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59]>O.CN(C)C=O>[Si:58]([O:25][C@H:17]1[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@H:15]([CH2:14][CH2:13][C@@H:12]3[C@@H:22]2[CH2:23][CH2:24][C@@:7]2([CH3:8])[C@:9]3([OH:26])[CH2:10][CH2:11][C@@H:6]2[C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)[CH2:16]1)([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59]

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1606964617beta-(3-Furyl)-5beta,14beta-androstane-3beta,14beta-diolHCID 8674878814beta,15beta-Epoxy-17beta(3-furyl)-5beta-androstan-3beta-ol

Produkt 1

HCID 700458673beta-Tert-butyldimethylsilyloxy-17beta-(3-furyl)-5beta-androstan-14beta-olAusbeute 113,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 10 g of 17β-(3-furyl)-5β-androstane-3β,14β-diol (II-a: Ref. comp.) (Minato H. and Nagasaki T., J. Chem. Soc. (C), 1966, 377)in 80 ml of dimethylformamide, 18 g of imidazole and 20.0 g of t-butyldimethylsilyl chloride were added at 0° C. After 12 hrs the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure and 15 g of crude 3β-tert-butyldimethylsilyloxy-17β-(3-furyl)-5β-androstan-14β-ol were obtained. A suspension of this protected alcohol and 1.3 g of KH in 75 ml of tetrahydrofuran was heated at 70° C. for an hr; then 2.7 g of methyl iodide were added. After 30' the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to give 12 g of 3β-tert-butyldimethylsilyloxy-14β-methoxy-17β-(3-furyl)-5β-androstane as a white amorphous solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cbae3cf7c8494d35a3c185b5b209c0c5
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05432169

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