Dimethylformamide → 3-Morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde

HRID 44254노트

반응식

HRID 44254 반응식
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[NH:11]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:12]1.C([O-])(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl>[N:17]1([CH2:16][C:13]2[CH:14]=[CH:15][NH:11][C:12]=2[CH:4]=[O:5])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 575870184-(1H-Pyrrol-3-ylmethyl)-morpholine

생성물 1

HCID 866508243-Morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a solution of DMF (66 mmoles) in DCM there is added, dropwise, at 0° C., POCl3. After stirring for 5 minutes, a solution of the compound obtained in Step B (33 mmoles) in DCM (60 ml) is added dropwise. After stirring for 4 hours at 0° C. and for 30 minutes at reflux, an aqueous solution of sodium acetate (110 mmoles) is added. After a further 30 minutes at reflux, aqueous 2M sodium hydroxide solution is added at ambient temperature until the pH is alkaline (9-10). The solution is stirred for 2 hours at ambient temperature, and then 300 ml of DCM are added. After extracting with DCM, the organic phase is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue obtained is purified by flash chromatography on silica gel (SiO2; gradient DCM/AcOEt) to yield the title product.

후처리

  1. customat 0° C.
  2. stirringAfter stirring for 4 hours at 0° C. and for 30 minutes
  3. temperatureat reflux
  4. temperatureAfter a further 30 minutes at reflux
  5. stirringThe solution is stirred for 2 hours at ambient temperature
  6. extractionAfter extracting with DCM
  7. washthe organic phase is washed with water and with saturated aqueous NaCl solution
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe residue obtained
  12. customis purified by flash chromatography on silica gel (SiO2; gradient DCM/AcOEt)

출처 및 근거

ORD 기록
ord-a27ccf32082843b3abb7f8f29a8680ab
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541412B2

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