Sodium Methoxide → (R)-tert-butyl 3-((5-cyano-6-methoxypyridin-2-yl)(methyl)amino)pyrrolidine-1-carboxylate

HRID 527908Notes

Reaction equation

HRID 527908 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:21])[C@@H:9]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]2)[CH:5]=[CH:4][C:3]=1[C:22]#[N:23].[CH3:24][O-:25].[Na+]>CO>[C:22]([C:3]1[CH:4]=[CH:5][C:6]([N:8]([CH3:21])[C@@H:9]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]2)=[N:7][C:2]=1[O:25][CH3:24])#[N:23]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86692137HCID 86692137, compound

Product 1

HCID 86692138(R)-tert-butyl 3-((5-cyano-6-methoxypyridin-2-yl)(methyl)amino)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (R)-tert-butyl 3-((6-chloro-5-cyanopyridin-2-yl)(methyl)amino)pyrrolidine-1-carboxylate (0.45 mmol) in MeOH (20 mL) was added the solution of NaOMe (0.9 mmol) in MeOH (2 mL). The reaction mixture was stirred at room temperature for 3 hours, then heated to 50° C., stirred for another 2 hours, then stirred at reflux overnight. The mixture was concentrated, diluted with EtOAc, washed with brine, dried, filtered, and concentrated to give the title compound.

Workup

  1. temperatureheated to 50° C.
  2. stirringstirred for another 2 hours
  3. stirringstirred
  4. temperatureat reflux overnight
  5. concentrationThe mixture was concentrated
  6. additiondiluted with EtOAc
  7. washwashed with brine
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c98f830418dd46c8a0b2b3e5e7438186
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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