Methanol → 3-O-Benzyl Estradiol

HRID 1243299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243299
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C@@H:18]([OH:27])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 11132151(8R,9S,13S,14S)-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one

Produkt 1

HCID 112914133-O-Benzyl Estradiol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 3-benzyloxyestra-1,3,5(10)-trien-17-one BLE99049 (3.46 g, 9.59 mmol) in THF (15 ml) and MeOH (38 ml) was added sodium borohydride (0.36 g, 9.58 mmol) at 0° C. The reaction mixture was stirred for 30 min at room temperature, then quenched with 10 ml of saturated aqueous NH4Cl and 50 ml of H2O added. The precipitate was collected by filtration and washed with H2O to afford 3.50 g of 3-benzyloxyestra-1,3,5(10)-trien-17β-ol BLE99051 (100% crude yield) as a white solid.

Aufarbeitung

  1. customquenched with 10 ml of saturated aqueous NH4Cl and 50 ml of H2O
  2. additionadded
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with H2O

Quellen und Nachweise

ORD-Eintrag
ord-6340ce760315406ca1e4b1a8c9ea64fe
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119081B2

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