Triphenylphosphine → 9-(3,17beta-dihydroxyoestra-1,3,5(10)-trien-7alpha-yl)-N-methyl-nonanamide

HRID 543016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 543016
BrCCCCCCCC(NC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br-].C(CCCCCCCCC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(O)=O.C([O:71][C:72]1[CH:89]=[CH:88][C:87]2[C@@H:86]3[C@H:77]([C@H:78]4[C@@:82]([CH2:84][CH2:85]3)([CH3:83])[C@@H:81]([OH:90])[CH2:80][CH2:79]4)[C@H:76]([CH:91]=[CH:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][C:99]([NH:101][CH3:102])=[O:100])[CH2:75][C:74]=2[CH:73]=1)C1C=CC=CC=1>>[OH:71][C:72]1[CH:89]=[CH:88][C:87]2[C@@H:86]3[C@H:77]([C@H:78]4[C@@:82]([CH2:84][CH2:85]3)([CH3:83])[C@@H:81]([OH:90])[CH2:80][CH2:79]4)[C@H:76]([CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][C:99]([NH:101][CH3:102])=[O:100])[CH2:75][C:74]=2[CH:73]=1

Komponenten

5

Edukt 4

HCID 11776TriphenylphosphineHCID 18795071(9-Carboxynonyl)(triphenyl)phosphanium bromideHCID 202068368-bromo-N-methyloctanamideHCID 867414419-(3-benzyloxy-17beta-hydroxyoestra-1,3,5(10)trien-7alpha-yl)-N-methylnon-8-enamide

Produkt 1

HCID 704467659-(3,17beta-dihydroxyoestra-1,3,5(10)-trien-7alpha-yl)-N-methyl-nonanamide

Versuchsvorschrift

The procedure described in the last paragraph of Example 6 was repeated except that (7-N-methylcarbamoylheptyl)triphenylphosphonium bromide (prepared from 8-bromo-N-methyloctanamide and triphenylphosphine by a similar process to that described in the last part of Example 22) was used in place of (9-carboxynonyl)triphenylphosphonium bromide. The hydrogenation process described in the second paragraph of Example 6 was then repeated using the 9-(3-benzyloxy-17β-hydroxyoestra-1,3,5(10)trien-7α-yl)-N-methylnon-8-enamide thus obtained as starting material, and there was thus obtained as an oil 9-(3,17β-dihydroxyoestra-1,3,5(10)-trien-7α-yl)-N-methyl-nonanamide, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Aufarbeitung

  1. customthus obtained

Quellen und Nachweise

ORD-Eintrag
ord-a71ec59b3a804b9f96adaeabac768efb
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659516

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