(7a,17b)-7-(9-Bromononyl)estra-1,3,5(10)-triene-3,17-diol Chemical Properties

Boiling point:

586.1±50.0 °C(Predicted)

Density 

1.196

storage temp. 

Sealed in dry,Room Temperature

pka

10.27±0.70(Predicted)

InChIKey

ILWDBZWOZQESSY-RIVKPNGLNA-N

SMILES

C([C@@H]1CC2=CC(O)=CC=C2[C@@]2([H])CC[C@@]3([C@@H](O)CC[C@@]3([H])[C@]12[H])C)CCCCCCCCBr |&1:1,10,14,15,19,21,r|

(7a,17b)-7-(9-Bromononyl)estra-1,3,5(10)-triene-3,17-diol Usage And Synthesis

Uses

(7a,17b)-7-(9-Bromononyl)estra-1,3,5(10)-triene-3,17-diol is used in the synthetic preparation of 7α-alkylated 19-norsteroids.

Definition

(7a,17b)-7-(9-Bromononyl)estra-1,3,5(10)-triene-3,17-diol is a Fulvestrant intermediate.

Synthesis

Synthesis of (7R,8R,9S,13S,14S,17S)-7-(9-bromononyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a ]phenanthrene-3,17-diol was performed in the following general steps: the compound of Formula II (5.0 g) prepared in Example 1 was added to a reaction flask with methanol (50 mL) and heated until dissolved. Subsequently, aqueous hydrobromic acid (5 mL of 40 mL) was slowly added and the reaction was carried out at 60 °C for 2 hours. After completion of the reaction, it was cooled to room temperature and the solid product was collected by filtration. The resulting solid was dried in a vacuum oven at 40 °C for 8 h to afford the compound of formula III (4.3 g), which was tested to be 97.7% pure.

References

[1] Patent: US2006/30552, 2006, A1. Location in patent: Page/Page column 25
[2] Patent: CN107325143, 2017, A. Location in patent: Paragraph 0010; 0011; 0012