Reaktion #997187

ord-1356ed6f810e4a77bc5aa66a55a38320

Reaktionsgleichung

CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C
pregnenolone
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C
1-((3S,8S,9S,10R,13S,14S,17S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3-[(1,1-dimethylethyl)dimethylsilyloxy]-10,13-dimethyl-1H-cyclopenta[α]phenanthren-17-yl)ethanone
C=C(C)CCCBr
5-bromo-2-methyl-1-pentene
C=C(C)CCCBr
5-Bromo-2-methyl-1-pentene
[I-].[I-].[Sm+2]
samarium diiodide
→
C=C(C)CCC[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C
20S-hydroxy steroid
Ausbeute 71.0%
C=C(C)CCC[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C
(3S,8S,9S,10R,13S,14S,17S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3-[(1,1-dimethylethyl)dimethylsilyloxy]-17-((S)-2-hydroxy-6-methylhept-6-en-2-yl) -10,13-dimethyl-1H-cyclopenta[α]phenanthrene
Ausbeute 71.0%

Edukte

CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C
pregnenolone
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C
1-((3S,8S,9S,10R,13S,14S,17S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3-[(1,1-dimethylethyl)dimethylsilyloxy]-10,13-dimethyl-1H-cyclopenta[α]phenanthren-17-yl)ethanone
C=C(C)CCCBr
5-bromo-2-methyl-1-pentene
C=C(C)CCCBr
5-Bromo-2-methyl-1-pentene
[I-].[I-].[Sm+2]
samarium diiodide

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeas described for the preparation of 2

Vorschrift

The coupling reaction of the protected pregnenolone 1 (500.0 mg, 1.16 mmol) with 5-bromo-2-methyl-1-pentene 9 (199.0 mg, 1.22 mmol) in the presence of samarium diiodide was performed under similar condition as described for the preparation of 2 to afford the 20S-hydroxy steroid 10 (419.0 mg, 0.82 mmol, 71%) as a white powder.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08022052B2uspto-grants-2011_09