Trioxobis(pyridine)chromium → 17beta-Formyl-6-t-butylcarboxy-6-azaandrost-4-en-3-one

HRID 1077592

Reaktionsgleichung

Reaktionsgleichung von HRID 1077592
[OH:1][CH2:2][C@H:3]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:22]([CH2:23][CH2:24][C@:4]12[CH2:5][C:6]([OH:8])=[O:7])[C@:20]1([CH3:21])[C:15](=[CH:16][C@@H:17]([OH:25])[CH2:18][CH2:19]1)[N:14]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:13]3.O=[Cr](=O)=O.C1C=CC=CN=1.C1C=CC=CN=1>C(Cl)Cl>[CH:2]([C@H:3]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:22]([CH2:23][CH2:24][C@:4]12[CH2:5][C:6]([OH:8])=[O:7])[C@:20]1([CH3:21])[C:15](=[CH:16][C:17](=[O:25])[CH2:18][CH2:19]1)[N:14]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:13]3)=[O:1]

Komponenten

4

Edukt 2

HCID 88565Trioxobis(pyridine)chromiumHCID 8674970617beta-Hydroxymethyl-3beta-hydroxy-6-t-butylcarboxy-6-azaandrost-4-ene

Produkt 1

HCID 8674970717beta-Formyl-6-t-butylcarboxy-6-azaandrost-4-en-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 17β-hydroxymethyl-3β-hydroxy-6-t-butylcarboxy-6-azaandrost-4-ene (182 mg, 0.448 mmol), prepared in part A above, in methylene chloride (7 mL) is added to freshly prepared Collins' reagent. (CrO3 ·2 pyridine) in methylene chloride (12 mL) at 0° C. After 15 minutes the solvent is decanted from the tar, the tar is triturated with methylene chloride (2×30 mL), the combined methylene chloride washed with 2N NaOH, saturated aqueous NaHSO4, saturated aqueous NaCl, dried over MgSO4, concentrated and chromatographed on silica gel (50% ehtyl acetate/hexanes) to give crude 17β-formyl-6-t-butylcarboxy-6-azaandrost-4-en-3-one of sufficient purity to carry on to the following steps; yield: 125 mg (69%).

Aufarbeitung

  1. customat 0° C
  2. customAfter 15 minutes the solvent is decanted from the tar
  3. customthe tar is triturated with methylene chloride (2×30 mL)
  4. washthe combined methylene chloride washed with 2N NaOH, saturated aqueous NaHSO4, saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customchromatographed on silica gel (50% ehtyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0866944a5af14269a04e364477c39829
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05543406

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