Methanol → HCID 59536666, compound

HRID 1922185Notes

Reaction equation

HRID 1922185 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([O:9][CH:10]([C@H:14]2[CH2:18][CH2:17][NH:16][CH2:15]2)[CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.[CH3:19][OH:20].[H-].[Na+]>CS(C)=O>[CH3:19][O:20][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([O:9][CH:10]([C@H:14]2[CH2:18][CH2:17][NH:16][CH2:15]2)[CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 59536658HCID 59536658, compound

Product 1

HCID 59536666HCID 59536666, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

Add (3S)-3-(1-(6-chloro-2-methyl-3-pyridyloxy)-butyl)-pyrrolidine (S-2) (0.65 g, 2.44 mmol), DMSO (9.75 mL), methanol (0.493 mL, 12.18 mmol), and sodium hydride (0.390 g, 9.75 mmol) to a reaction vial. Evacuate the vial and purge with nitrogen. Heat the mixture at 100° C. over night. Pour the reaction mixture onto an SCX column and rinse with methanol. Attach the SCX column on top of a silica gel column and elute with 5-30% of NH3OH/ethanol (1:9) in chloroform to obtain 0.420 g (65%) of (3S)-3-(1-(6-methoxy-2-methyl-3-pyridyloxy)-butyl)-pyrrolidine

Workup

  1. customto a reaction vial
  2. customEvacuate the vial and
  3. custompurge with nitrogen
  4. additionPour the reaction mixture onto an SCX column
  5. washrinse with methanol
  6. washelute with 5-30% of NH3OH/ethanol (1:9) in chloroform

Sources & evidence

ORD record
ord-9f04c7c4e6c34ac086c7ee8379dad7f7
Source dataset
uspto-grants-2012_05
Patent number
US08173821B2

Reaction notes

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