Methanol → HCID 18638591, compound

HRID 2073456Notes

Reaction equation

HRID 2073456 reaction equation
[CH3:1][C@@:2]12[C:10](=O)[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=3[C@H:5]1[CH2:4][CH2:3]2.[C:22]([BH3-])#[N:23].[Na+].[CH3:26][OH:27].[O:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1.C(O[CH2:37][CH3:38])(=O)C>>[OH:28][C:32]1[CH:38]=[CH:37][C:29]([CH2:22][NH:23][C@H:10]2[CH2:9][CH2:8][C@H:7]3[C@H:6]4[C@H:5]([CH2:4][CH2:3][C@:2]23[CH3:1])[C:15]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=2[CH2:13][CH2:12]4)=[CH:30][C:31]=1[O:27][CH3:26]

Participants

6

Reactant 5

HCID 887MethanolHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 92895(+)-Estrone 3-methyl etherHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18638591HCID 18638591, compound

Procedure

4-Hydroxy-3-methoxybenzylhydrochloride amine (8.32 g), estrone methyl ether (2.51 g), sodium cyanoborohydride (0.55 g) were added to methanol (30 ml) followed by tetrahydrofuran (22 ml). The solution was allowed to stir for hour 4 days at room temperature. TLC (ethyl acetate) revealed the formation of a more polar compound and the presence of some starting material. The solution was heated to reflux for a few more days. TLC revealed the reaction did not complete. Excess solvent was removed at reduced pressure. Water was added and made basic (pH 9) with aqueous 50% NaOH. The solution was extracted with ether (3X). The combined extracts were dried (Na2SO4), filtered and concentrated. The oil was mixed with 20 g of flash silica gel and ethyl acetate. The solvent was removed under reduced pressure and the silica gel was poured on top of the chromatographic column. The compound was eluted with ethyl acetate. The title compound was obtained as a solid and was recrystallized from ethyl acetate (0.488 g), mp 169°-169.5° C. (PLA2, diabetes-)

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for a few more days
  3. customExcess solvent was removed at reduced pressure
  4. additionWater was added
  5. extractionThe solution was extracted with ether (3X)
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. additionThe oil was mixed with 20 g of flash silica gel and ethyl acetate
  10. customThe solvent was removed under reduced pressure
  11. additionthe silica gel was poured on top of the chromatographic column
  12. washThe compound was eluted with ethyl acetate

Sources & evidence

ORD record
ord-5812587208844882814eda8f4550c5b0
Source dataset
uspto-grants-1990_04
Patent number
US04917826

Reaction notes

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