HCID 86672436, compound → tert-butyl 2-(6-(methoxycarbonyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate

HRID 41217Notes

Reaction equation

HRID 41217 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][C@H:29]([CH3:33])[CH2:28]1)=[CH:9][C:8]2=[O:34])=[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][C@H:29]([CH3:33])[CH2:28]1)=[CH:9][C:8]2=[O:34])=[O:4]

Participants

4

Reactant 1

HCID 86672436HCID 86672436, compound

Product 1

HCID 86672437tert-butyl 2-(6-(methoxycarbonyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylateYield 59%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalyst2×HCID 887MethanolSolvent

Procedure

(R)-tert-Butyl 2-(6-(methoxycarbonyl)-2-(2-methylmorpholino)-4-oxo-4H-chromen-8-yl)-1H-pyrrole-1-carboxylate (2 g, 4.27 mmol) and 5% Rhodium on Alumina (50% wet) (0.4 g, 0.09 mmol) in MeOH (50 mL) were stirred under an atmosphere of hydrogen at 5 bar and 65° C. for 2 h. More catalyst was added and stirring continued overnight. 2 g of 5% Rh/C was then added followed by the same amount after 1 h then after another 2 h. The catalyst was filtered through celite and washed with MeOH/DCM and the solvent evaporated. The crude product was purified by flash chromatography on silica gel eluting with 10 to 15% MeOH in EtAc. The solvent was evaporated to dryness to afford tert-butyl 2-(6-(methoxycarbonyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate (1.18 g, 59%) as a white solid. Mass Spectrum: m/z [M+H]+=473.

Workup

  1. additionMore catalyst was added
  2. waitfollowed by the same amount after 1 h
  3. waitafter another 2 h
  4. filtrationThe catalyst was filtered through celite
  5. washwashed with MeOH/DCM
  6. customthe solvent evaporated
  7. customThe crude product was purified by flash chromatography on silica gel eluting with 10 to 15% MeOH in EtAc
  8. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-b857934df5194e0d921e9780b344244e
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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