Triethylamine → methyl 2-(2-methoxy-2-oxoethyl)-5,6,7,8-tetrahydro-2H-[1,2,4]oxadiazolo[2,3-a]pyridine-2-carboxylate

HRID 2219040Notes

Reaction equation

HRID 2219040 reaction equation
Cl.[NH:2]=[C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[OH:9].C(N(CC)CC)C.[C:17]([C:23]([O:25][CH3:26])=[O:24])#[C:18][C:19]([O:21][CH3:22])=[O:20]>C(Cl)(Cl)Cl>[CH3:22][O:21][C:19](=[O:20])[CH2:18][C:17]1([C:23]([O:25][CH3:26])=[O:24])[O:9][N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:3]2=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12980Dimethyl acetylenedicarboxylateHCID 671477972-Iminopiperidin-1-ol hydrochloride

Product 1

HCID 59771060methyl 2-(2-methoxy-2-oxoethyl)-5,6,7,8-tetrahydro-2H-[1,2,4]oxadiazolo[2,3-a]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-iminopiperidin-1-ol hydrochloride in chloroform was added triethylamine. The mixture was stirred for 5 min. at room temperature, then cooled to 0° C. and 1.2 eq. of dimethyl acetylenedicarboxylate were added dropwise under stirring. The cooling bath was removed and the mixture was stirred at room temperature for one hour. The solvent was removed under reduced pressure and the solution was partitioned between ethyl acetate and half saturated aq. ammonium chloride. The aqueous phase was further extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and filtered through silica gel. The solvent was removed under vacuum to afford methyl 2-(2-methoxy-2-oxoethyl)-5,6,7,8-tetrahydro-2H-[1,2,4]oxadiazolo[2,3-a]pyridine-2-carboxylate as a light yellow oil.

Workup

  1. temperaturecooled to 0° C.
  2. stirringunder stirring
  3. customThe cooling bath was removed
  4. stirringthe mixture was stirred at room temperature for one hour
  5. customThe solvent was removed under reduced pressure
  6. customthe solution was partitioned between ethyl acetate and half saturated aq. ammonium chloride
  7. extractionThe aqueous phase was further extracted with ethyl acetate
  8. dry with materialThe combined organic phases were dried over sodium sulfate
  9. filtrationfiltered through silica gel
  10. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-bfd00a4af08d4424b33ef2d933cc1be1
Source dataset
uspto-grants-2008_08
Patent number
US07414045B2

Reaction notes

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