Reaktion #684622

ord-ce7257e7003f4e99b1e7535e164b02fd

Reaktionsgleichung

C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
dehydroepiandrosterone
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
pregnenolone
CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
progesterone
C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@H]43)[C@@H]1CCC2=O
3β-hydroxy-estr-5-en-17-one
C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
5α-androstane-3,17-dione
C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@@H]2O
androst-5-ene-3β,17β-diol
C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@H]43)[C@@H]1CC[C@@H]2O
estr-5-en-3β,17β-diol
C[C@]12CC[C@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
5α-androstane-3β,17β-diol
→
C[C@]12C[C@H](O)[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O
estra-1,3,5(10)-triene-3,11β,17β-triol

Edukte

—
succinates
—
11α-hydroxy succinate
—
pregn-5-ene-3β,20α
—
diols
—
pregn-4-ene-3,20α
—
diols
C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
dehydroepiandrosterone
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
pregnenolone
CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
progesterone
C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@H]43)[C@@H]1CCC2=O
3β-hydroxy-estr-5-en-17-one
C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
5α-androstane-3,17-dione
C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@@H]2O
androst-5-ene-3β,17β-diol
C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@H]43)[C@@H]1CC[C@@H]2O
estr-5-en-3β,17β-diol
C[C@]12CC[C@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
5α-androstane-3β,17β-diol

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

This reduction procedure is useful for the preparation of the 11α-acid succinates of 11α-hydroxy analogs of dehydroepiandrosterone, pregnenolone, progesterone, 3β-hydroxy-estr-5-en-17-one, and 5α-androstane-3,17-dione to 11α-hydroxy succinate derivatives of androst-5-ene-3β,17β-diol, pregn-5-ene-3β,20α and 20β diols, pregn-4-ene-3,20α and 20β diols, estr-5-en-3β,17β-diol and 5α-androstane-3β,17β-diol.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04013688uspto-grants-1977_03