tert-butyl 2-(6-(morpholine-4-carbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)-2,3-dihydro-1H-pyrrole-1-carboxylate → tert-butyl 2-(6-(morpholine-4-carbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate

HRID 41203Notes

Reaction equation

HRID 41203 reaction equation
[N:1]1([C:7]([C:9]2[CH:10]=[C:11]3[C:16](=[C:17]([CH:19]4[CH2:23][CH:22]=[CH:21][N:20]4[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:18]=2)[O:15][C:14]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[CH:13][C:12]3=[O:37])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N1(C(C2C=C3C(=C(C4C=CCN4C(OC(C)(C)C)=O)C=2)OC(N2CCOCC2)=CC3=O)=O)CCOCC1>C(O)C.[Pt](=O)=O>[N:1]1([C:7]([C:9]2[CH:10]=[C:11]3[C:16](=[C:17]([CH:19]4[CH2:23][CH2:22][CH2:21][N:20]4[C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[CH:18]=2)[O:15][C:14]([N:31]2[CH2:32][CH2:33][O:34][CH2:35][CH2:36]2)=[CH:13][C:12]3=[O:37])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 86672426tert-butyl 2-(6-(morpholine-4-carbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)-2,3-dihydro-1H-pyrrole-1-carboxylateHCID 86672427tert-butyl 2-(6-(morpholine-4-carbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 86672425tert-butyl 2-(6-(morpholine-4-carbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

The above mixture of tert-butyl 2-(6-(morpholine-4-carbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)-2,3-dihydro-1H-pyrrole-1-carboxylate compound and tert-butyl 2-(6-(morpholine-4-carbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (1:1) (2.1 g, 2.05 mmol) and platinum(IV) oxide (0.093 g, 0.41 mmol) in ethanol (30 ml) was hydrogenated under 1.2 atm at room temperature for 4 h. The resulting solution was filtered and the filtrate was concentrated to dryness to afford the crude tert-butyl 2-(6-(morpholine-4-carbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate (1.60 g, 76%) as an orange solid. Mass Spectrum: m/z [M+H]+=514.

Workup

  1. filtrationThe resulting solution was filtered
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-61ae2a2d2d4b44a2838ba9cca6a279ce
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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