tert-butyl 2-(6-(methoxycarbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)-1H-pyrrole-1-carboxylate → tert-butyl 2-(6-(methoxycarbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate

HRID 41167Notes

Reaction equation

HRID 41167 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([C:15]3[N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:17]=[CH:18][CH:19]=3)[CH:14]=1)[O:11][C:10]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[CH:9][C:8]2=[O:33])=[O:4]>CO.[Rh]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([CH:15]3[CH2:19][CH2:18][CH2:17][N:16]3[C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])[CH:14]=1)[O:11][C:10]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[CH:9][C:8]2=[O:33])=[O:4]

Participants

4

Reactant 1

HCID 86672403tert-butyl 2-(6-(methoxycarbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)-1H-pyrrole-1-carboxylate

Product 1

HCID 86672404tert-butyl 2-(6-(methoxycarbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylateYield 83.5%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

tert-butyl 2-(6-(methoxycarbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)-1H-pyrrole-1-carboxylate (17.1 g, 37.63 mmol) and 5% Rhodium on Alumina (50% wet) (3.4 g, 0.80 mmol) in MeOH (175 mL) were stirred under an atmosphere of hydrogen at 5 bars and 65° C. for 7 h. The catalyst was removed from the reaction by filtration on a pad of Celite and washed with MeOH. The celite and catalyst were slurried in 500 mL of 10% MeOH in DCM and filtered again. The organic solutions were combined and evaporated to give tert-butyl 2-(6-(methoxycarbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate (14.4 g, 83%) as a fawn solid.

Workup

  1. customThe catalyst was removed from the reaction by filtration on a pad of Celite
  2. washwashed with MeOH
  3. filtrationfiltered again
  4. customevaporated

Sources & evidence

ORD record
ord-648bf7c1e9e243e7a4eff7fbd276f4b5
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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