Formaldehyde → (S)-Methyl 1-methylpyrrolidine-2-carboxylate

HRID 21755

반응식

HRID 21755 반응식
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[CH2:9]=[O:10].[BH4-].[Na+].[C:13]([O-])([O-])=O.[K+].[K+]>CO>[CH3:9][O:10][C:3](=[O:5])[C@@H:2]1[CH2:6][CH2:7][CH2:8][N:1]1[CH3:13]

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 4311764Sodium borohydride

생성물 1

HCID 10920622(S)-Methyl 1-methylpyrrolidine-2-carboxylate

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

The L-proline is dissolved in methanol, the solution is cooled to 0° C. and 36% aqueous formaldehyde is added with stirring. To this solution is then added powdered NaBH4 in portions while maintaining the temperature between -5° and +5° C. The reaction is filtered, the filter cake extracted with solvent and combined with the filtrate, and the solvents evaporated to dryness. The residual N-methyl-L-proline is then dissolved in and reacted with methanol in the presence of H2SO4 at reflux for 4-24 hr. The reaction mixture is cooled to 0° C., and with vigorous stirring a solution of K2CO3 is slowly added to the mixture, until the pH is between pH 7 and 8, then the title product is extracted from the basic mixture and isolated after drying and removal of the solvent.

후처리

  1. additionTo this solution is then added
  2. temperaturewhile maintaining the temperature between -5° and +5° C
  3. filtrationThe reaction is filtered
  4. extractionthe filter cake extracted with solvent
  5. customthe solvents evaporated to dryness
  6. dissolutionThe residual N-methyl-L-proline is then dissolved in and
  7. customreacted with methanol in the presence of H2SO4
  8. temperatureat reflux for 4-24 hr
  9. temperatureThe reaction mixture is cooled to 0° C.
  10. additionis slowly added to the mixture, until the pH
  11. extractionthe title product is extracted from the basic mixture
  12. customisolated
  13. customafter drying
  14. customremoval of the solvent

출처 및 근거

ORD 기록
ord-f35bf35630634bafb7fa2eff30a2d559
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424444

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