Potassium Carbonate → (S)-methyl 5-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)picolinate

HRID 407990Notes

Reaction equation

HRID 407990 reaction equation
CS([O:5][C@@H:6]1[CH2:10][CH2:9][N:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[C:7]1=[O:24])(=O)=O.O[C:26]1[CH:27]=[CH:28][C:29]([C:32]([O:34][CH3:35])=[O:33])=[N:30][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][CH:11]([N:8]2[CH2:9][CH2:10][C@H:6]([O:5][C:26]3[CH:27]=[CH:28][C:29]([C:32]([O:34][CH3:35])=[O:33])=[N:30][CH:31]=3)[C:7]2=[O:24])[CH2:12][CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4715126Methyl 5-hydroxypyridine-2-carboxylateHCID 86688072(R)-tert-butyl 4-(3-(methylsulfonyloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

Product 1

HCID 67469865(S)-methyl 5-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)picolinateYield 81.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

(R)-tert-Butyl 4-(3-(methylsulfonyloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (Preparation D; 0.20 g, 0.55 mmol) was added to a mixture of methyl 5-hydroxypicolinate (0.10 g, 0.66 mmol), and potassium carbonate (0.099 g, 0.72 mmol) in DMF (1.6 mL). The mixture was stirred at 60° C. overnight and then cooled to ambient temperature. The mixture was partitioned between saturated aqueous NH4Cl (40 mL) and EtOAc (100 mL). The organic phase was washed successively with water (40 mL), water (40 mL) and brine (40 mL). The combined organic phases were dried over MgSO4, filtered and concentrated. The residue was purified on silica (eluting with EtOAc) to afford (S)-methyl 5-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)picolinate (0.19 g, 0.45 mmol, 81%).

Workup

  1. temperaturecooled to ambient temperature
  2. customThe mixture was partitioned between saturated aqueous NH4Cl (40 mL) and EtOAc (100 mL)
  3. washThe organic phase was washed successively with water (40 mL), water (40 mL) and brine (40 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica (eluting with EtOAc)

Sources & evidence

ORD record
ord-d8fcf4c93fba41f78cdddd3b4cb9be2a
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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