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Water → 13-Methyl-16-(3,4,5-trimethoxy-benzylidene)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

HRID 1675923
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1675923
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]3[CH:14]([CH2:15][CH2:16][C:17]=2[CH:18]=1)[CH:13]1[C:9]([CH3:33])([C:10](=[O:32])[C:11](=[CH:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=2)[CH2:12]1)[CH2:8][CH2:7]3.[BH4-].[Na+].C(OCC)(=O)C.O>C1COCC1.CO>[CH3:33][C:9]12[CH2:8][CH2:7][CH:6]3[CH:14]([CH2:15][CH2:16][C:17]4[CH:18]=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=43)[CH:13]1[CH2:12][C:11](=[CH:19][C:20]1[CH:21]=[C:22]([O:30][CH3:31])[C:23]([O:28][CH3:29])=[C:24]([O:26][CH3:27])[CH:25]=1)[CH:10]2[OH:32]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 50130353-Hydroxy-13-methyl-16-(3,4,5-trimethoxy-benzylidene)-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

Produkt 1

HCID 6734972913-Methyl-16-(3,4,5-trimethoxy-benzylidene)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-Hydroxy-13-methyl-16-(3,4,5-trimethoxy-benzylidene)-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one (448 mg, 1.0 mmol, CAB01124) in THF/methanol (1:1, 40 ml) was cooled to 0° C. (ice bath) and sodium borohydride (100 mg, 2.64 mmol) was added. The reaction mixture was stirred for 2 h at this temperature, while it was turning from slightly yellow to colourless. The solution was transferred into a separation funnel and ethyl acetate (100 ml) and water (100 ml) were added. The organic layer was separated, washed with water (50 ml) and brine (50 ml), dried over sodium sulphate and concentrated under reduced pressure. Yield 445 mg (99%) white solid. 1H-NMR (CDCl3, 400 MHz), δ: 0.74 (s, 3H), 1.20-1.60 (m, 6H), 1.90-1.98 (m, 1H), 2.01-2.08 (m, 1H), 2.21-2.41 (m, 3H), 2.74-2.90 (m, 3H), 3.86 (s, 3H), 3.89 (s, 6H), 4.15 (d, J=9.4 Hz, 1H, H-17), 4.62 (s, 1H, —OH), 6.49-6.51 (m, 1H), 6.59 (d, J=2.3 Hz, 1H), 6.63-6.68 (m, 3H), 7.18 (d, J=8.2 Hz, 1H). LRMS (FAB+): 451.3 (100, [M+H]+).

Aufarbeitung

  1. additionwas added
  2. customThe solution was transferred into a separation funnel
  3. customThe organic layer was separated
  4. washwashed with water (50 ml) and brine (50 ml)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3c8387cc64ab4c5ca79129382766d3e7
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08003783B2

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