2-Methoxyestradiol → HCID 68621641, compound

HRID 32298Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([OH:22])=[CH:5][C:6]2[CH2:7][CH2:8][C@@H:9]3[C@@H:18]([C:19]=2[CH:20]=1)[CH2:17][CH2:16][C@@:14]1([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]1O.C(N(S(F)(F)[F:29])CC)C>ClCCl>[F:29][C@@H:13]1[CH2:12][CH2:11][C@H:10]2[C@H:9]3[C@H:18]([CH2:17][CH2:16][C@:14]12[CH3:15])[C:19]1[CH:20]=[C:3]([O:2][CH3:1])[C:4]([OH:22])=[CH:5][C:6]=1[CH2:7][CH2:8]3

Participants

Conditions

Temperature: -35 °C

Procedure

215 mg of 2-methoxy-estra-1,3,5(10)-triene-3,17β-diol was dissolved in 20 ml of absolute dichloromethane and cooled to −35° C. Then, 280 μl of diethylamino sulfur trifluoride was added, and the cold bath was removed. After 1 hour, it was poured into aqueous sodium bicarbonate solution and extracted with dichloromethane (3×). The combined organic phases were dried and concentrated by evaporation in a rotary evaporator. Flash chromatography (cyclohexane/ethyl acetate=10:1) yielded 49% crude product, which was purified by means of HPLC (Chiracel OD-H 250×4.6 mm; n-heptane/2-propanol=95/5). 46 mg (21%) of 17α-fluoro-3-hydroxy-2-methoxy-estra-1,3,5(10)-triene was obtained as colorless crystals.

Workup

customthe cold bath was removed
additionit was poured into aqueous sodium bicarbonate solution
extractionextracted with dichloromethane (3×)
customThe combined organic phases were dried
concentrationconcentrated by evaporation in a rotary evaporator
customFlash chromatography (cyclohexane/ethyl acetate=10:1) yielded 49% crude product, which
customwas purified by means of HPLC (Chiracel OD-H 250×4.6 mm; n-heptane/2-propanol=95/5)

Sources & evidence

ORD record: ord-f29323239000469cbfcf960cb7b57b7e
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427610B2

Reaction notes

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