Methanol → N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-5-(2-hydroxyethylthio)pentanamide

HRID 52104노트

반응식

HRID 52104 반응식
[BH4-].[Na+].[N:3]1([CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([O:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][NH:21][C:22](=[O:33])[CH2:23][CH2:24][CH2:25][CH2:26][S:27][CH2:28][C:29](OC)=[O:30])[CH:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CO>O1CCCC1>[N:3]1([CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([O:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][NH:21][C:22](=[O:33])[CH2:23][CH2:24][CH2:25][CH2:26][S:27][CH2:28][CH2:29][OH:30])[CH:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

참가 물질

5

반응물 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 67725929N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-5-(methoxycarbonylmethylthio)pentanamide

생성물 1

HCID 67725636N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-5-(2-hydroxyethylthio)pentanamide수율 81.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

0.21 g of sodium borohydride was added to a solution of 1.98 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-5-(methoxycarbonylmethylthio)pentanamide [prepared as described in step (b) above] in 40 ml of tetrahydrofuran, and 8 ml of methanol were added dropwise to the mixture, whilst ice-cooling; it was then stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was mixed with water. The resulting aqueous mixture was extracted with ethyl acetate, and the extract was freed from the solvent by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:9 by volume mixture of methanol and methylene chloride as the eluent, to give 1.51 g (yield 63%) of the title compound as an oil.

후처리

  1. additionwere added dropwise to the mixture, whilst ice-
  2. temperaturecooling
  3. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  4. additionthe residue was mixed with water
  5. extractionThe resulting aqueous mixture was extracted with ethyl acetate
  6. distillationthe extract was freed from the solvent by distillation under reduced pressure
  7. customThe residue was purified by column chromatography through silica gel
  8. additionby volume mixture of methanol and methylene chloride as the eluent

출처 및 근거

ORD 기록
ord-27135af69dee4deda6036009f05f3ba6
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616579

반응 노트

불러오는 중…