Hydrochloric Acid → methyl 2-((R)-2-methylmorpholino)-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate

HRID 41218Notes

Reaction equation

HRID 41218 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([CH: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][C@H:30]([CH3:34])[CH2:29]1)=[CH:10][C:9]2=[O:35])=[O:5]>C(Cl)Cl>[CH3:34][C@@H:30]1[CH2:29][N:28]([C:11]2[O:12][C:13]3[C:8]([C:9](=[O:35])[CH:10]=2)=[CH:7][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:15][C:14]=3[CH:16]2[CH2:20][CH2:19][CH2:18][NH:17]2)[CH2:33][CH2:32][O:31]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86672437tert-butyl 2-(6-(methoxycarbonyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate

Product 1

HCID 86672438methyl 2-((R)-2-methylmorpholino)-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl 4N (6.24 mL, 24.97 mmol) was added to a stirred solution of tert-butyl 2-(6-(methoxycarbonyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate (1.18 g, 2.50 mmol) in DCM (10 mL) at room temperature and stirred for 16 h. the solvents were evaporated and DCM (5 mL) and MeOH (5 mL) were added followed by 10% methanolic ammonia (7 N) in dichloromethane (5 mL). The solid was filtered and washed with a 1:1 mixture of DCM and MeOH. The solvent was evaporated to dryness and the crude product was purified by flash chromatography on silica gel eluting with 0 to 10% MeOH in DCM. The solvent was evaporated to dryness, triturated with diethyl ether to give a solid which was collected by filtration and dried under vacuum to give methyl 2-((R)-2-methylmorpholino)-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (0.760 g, 82%) as a white solid. Mass Spectrum: m/z [M+H]=373.

Workup

  1. customwere evaporated
  2. additionDCM (5 mL) and MeOH (5 mL) were added
  3. filtrationThe solid was filtered
  4. washwashed with a 1:1 mixture of DCM and MeOH
  5. customThe solvent was evaporated to dryness
  6. customthe crude product was purified by flash chromatography on silica gel eluting with 0 to 10% MeOH in DCM
  7. customThe solvent was evaporated to dryness
  8. customtriturated with diethyl ether
  9. customto give a solid which
  10. filtrationwas collected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-c9b7fb0f65fa4c4e8c1cf45725e40a3c
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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