Reaktion #69446

ord-cf98abd219ca4358bf00f074d9ea0fbf

Reaktionsgleichung

Cl
Hydrogen chloride
COC(=O)c1cc(C2CCCN2C(=O)OC(C)(C)C)c2oc(N3CCOCC3)cc(=O)c2c1
tert-butyl 2-(6-(methoxycarbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate
ClCCl
DCM
COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1
methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate
Ausbeute 83.1%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe solvents were evaporated
  2. 2
    Sonstigethe residue azeotroped twice with MeCN
  3. 3
    Sonstigedried under vacuum at 50° C
  4. 4
    ExtraktionThe remaining solid was then extracted with DCM
  5. 5
    TrocknenThe DCM was dried over MgSO4
  6. 6
    Einengenconcentrated

Vorschrift

Hydrogen chloride (4M in dioxane) (2.4 mL, 9.6 mmol) was added to a stirred solution of tert-butyl 2-(6-(methoxycarbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate (440 mg, 0.96 mmol) dissolved in dioxane (3 mL) and DCM (3 mL) at room temperature and the reaction mixture stirred for 4 h. The solvents were evaporated and the residue azeotroped twice with MeCN and dried under vacuum at 50° C. The remaining solid was then extracted with DCM. The DCM was dried over MgSO4 and concentrated to afford methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (286 mg, 83%) as a pale beige solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08530470B2uspto-grants-2013_09