Hydrochloric Acid → methyl 2-morpholino-4-oxo-8-[(2R)-pyrrolidin-2-yl]chromene-6-carboxylate
Reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([C@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3C(OC(C)(C)C)=O)[CH:15]=1)[O:12][C:11]([N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)=[CH:10][C:9]2=[O:34])=[O:5]>C(Cl)Cl>[O:31]1[CH2:30][CH2:29][N:28]([C:11]2[O:12][C:13]3[C:8]([C:9](=[O:34])[CH:10]=2)=[CH:7][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:15][C:14]=3[C@H:16]2[CH2:20][CH2:19][CH2:18][NH:17]2)[CH2:33][CH2:32]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Hydrogen chloride (4M in dioxane) (8.81 mL, 35.22 mmol) was added to a stirred solution of tert-butyl (2R)-2-(6-(methoxycarbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate (1.90 g, 3.52 mmol) dissolved in DCM (15 mL) and the reaction mixture was stirred for 8 h at room temperature After concentration, 10% methanolic ammonia (7 N) in DCM was added, the reaction mixture was adsorbed on silica gel and then purified by flash chromatography on silica gel eluting with 0 to 8% methanolic ammonia (7 N) in DCM. The solvents were evaporated to dryness to afford after trituration with diethyl ether, methyl 2-morpholino-4-oxo-8-[(2R)-pyrrolidin-2-yl]chromene-6-carboxylate (1.11 g, 88%) as a light orange crystalline solid.
Workup
- concentrationAfter concentration, 10% methanolic ammonia (7 N) in DCM
- additionwas added
- custompurified by flash chromatography on silica gel eluting with 0 to 8% methanolic ammonia (7 N) in DCM
- customThe solvents were evaporated to dryness
Sources & evidence
- ORD record
- ord-05ec3ded8f2a4278867aa55134639bab
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08530470B2
Reaction notes
Loading…