Potassium Carbonate → HCID 66718399, compound

HRID 876956Notes

Reaction equation

HRID 876956 reaction equation
[O:1]1[CH2:5][CH2:4][C@H:3]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:19].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[O:1]1[CH2:5][CH2:4][C@H:3]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N+:9]=2[O-:19])[CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 70297m-Chloroperbenzoic acidHCID 66718431HCID 66718431, compound

Product 1

HCID 66718399HCID 66718399, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(Tetrahydrofuran-3-yloxymethyl)pyridine (110.33 g, 0.616 mol, 1 eq) was dissolved in 900 mL DCM and cooled in an ice bath. 3-Chloroperoxybenzoic acid (151.77 g, 0.677 mol, 1.1 eq) was added and the solution was warmed to room temperature and stirred overnight. K2CO3 (85.09 g, 0.616 mol, 1 eq) was added as a solid and stirred for 2 hours. The white precipitate was filtered off and the filter cake washed with dichloromethane. Another portion of K2CO3 (85.09 g, 0.616 mol, 1 eq) was added to the filtrate and stirred for 3 days. The white solid was filtered off and the filtrate evaporated to give the title compound (119.62 g, 99%) as a yellow oil; LC-MS Retention time 1.27 min; (M+H)+ 196.

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirred for 2 hours
  3. filtrationThe white precipitate was filtered off
  4. washthe filter cake washed with dichloromethane
  5. stirringstirred for 3 days
  6. filtrationThe white solid was filtered off
  7. customthe filtrate evaporated

Sources & evidence

ORD record
ord-88784b4ddad143609aff10817ae3352c
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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