Reaction #69482

Reaction equation

HCl

tert-butyl 2-(6-(morpholine-4-carbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate

→

6-(morpholine-4-carbonyl)-2-morpholino-8-(pyrrolidin-2-yl)-4H-chromen-4-one

Yield 62.2%

Solvents

DCM

Conditions

Workup

1. 1
   ConcentrationAfter concentration, DCM (15 mL) and MeOH (15 mL)
2. 2
   workup.ADDITIONwere added
3. 3
   Otherpurified by flash chromatography on silica gel eluting with 0 to 10% methanol in DCM
4. 4
   OtherThe solvent was evaporated to dryness
5. 5
   Otherto give a solid
6. 6
   Otherdried under vacuum

Procedure

HCl 4M (9.74 mL, 39 mmol) was added to a stirred solution of tert-butyl 2-(6-(morpholine-4-carbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate (2 g, 3.89 mmol) dissolved in DCM (15 mL) at r.t and stirred over the week-end. After concentration, DCM (15 mL) and MeOH (15 mL) were added, followed by a solution of 10% methanolic ammonia (7 N) in DCM (10 mL). The crude product was adsorbed on silica gel and purified by flash chromatography on silica gel eluting with 0 to 10% methanol in DCM. The solvent was evaporated to dryness to give a solid and dried under vacuum to give 6-(morpholine-4-carbonyl)-2-morpholino-8-(pyrrolidin-2-yl)-4H-chromen-4-one (1.0 g, 62%) as a beige solid. Mass Spectrum: m/z [M+H]+=414.

Source