Reaktion #70402

ord-b11b897c0b3d4a9f8168cae229286614

Reaktionsgleichung

C[C@]12CCC(=O)CC1C[C@@H](C(=O)O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
7α-carboxyandrostane-3,17-dione
CO
MeOH
CCN=C=NCCCN(C)C
EDAC
O
H2O
→
COC(=O)[C@@H]1CC2CC(=O)CC[C@]2(C)[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@H]12
title compound
COC(=O)[C@@H]1CC2CC(=O)CC[C@]2(C)[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@H]12
7α-Methoxycarbonylandrostane-3,17-dione

Edukte

C[C@]12CCC(=O)CC1C[C@@H](C(=O)O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
7α-carboxyandrostane-3,17-dione
CO
MeOH
CCN=C=NCCCN(C)C
EDAC
O
H2O

Reagenzien

CN(C)c1ccncc1
DMAP

Lösungsmittel

ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionthe mixture was extracted with CH2Cl2 (2×)
  2. 2
    WaschenThe combined organic extracts were washed with H2O, brine
  3. 3
    Trocknendried over Na2SO4
  4. 4
    Filtrationfiltered
  5. 5
    Sonstigeevaporated to dryness
  6. 6
    SonstigeThe residue was purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40)

Vorschrift

To a stirred solution of 7α-carboxyandrostane-3,17-dione (680 mg) in CH2Cl2 (30 mL) at 0° C., MeOH (160 μL), DMAP (20 mg) and EDAC (800 mg) were added. After stirring overnight at room temperature, H2O was added and the mixture was extracted with CH2Cl2 (2×). The combined organic extracts were washed with H2O, brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40) to give the title compound II-bc (500 mg, 70%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 3.63 (3H, s), 2.85 (1H, m), 2.50-0.75 (20H, m), 1.12 (3H, s), 0.86 (3H, s).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536160B2uspto-grants-2013_09