Chloroform → (R)-1-(11H-dibenz[b,f][1,4]oxathiepin-11-ylmethyl)-3-piperidinecarboxylic acid ethyl ester

HRID 1107272노트

반응식

HRID 1107272 반응식
Br[CH2:2][CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[S:4]1.C(C(C(C(O)=O)O)O)(O)=O.[CH2:28]([O:30][C:31]([C@@H:33]1[CH2:38][CH2:37][CH2:36][NH:35][CH2:34]1)=[O:32])[CH3:29].C(Cl)(Cl)Cl>C1C=CC=CC=1>[CH2:28]([O:30][C:31]([C@@H:33]1[CH2:38][CH2:37][CH2:36][N:35]([CH2:2][CH:3]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][C:6]3[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=3[S:4]2)[CH2:34]1)=[O:32])[CH3:29]

참가 물질

5

반응물 3

HCID 6212ChloroformHCID 2733695(R)-(-)-Ethyl Nipecotate TartrateHCID 1352205711-bromomethyl-11H-dibenz[b,f][1,4]oxathiepine

생성물 1

HCID 70293235(R)-1-(11H-dibenz[b,f][1,4]oxathiepin-11-ylmethyl)-3-piperidinecarboxylic acid ethyl ester수율 53%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A mixture of 11-bromomethyl-11H-dibenz[b,f][1,4]oxathiepine (6.15 g, 20 mmol, prepared similarly as described in Coll. Czech. Chem. Commun. 50, 1484, 1985), (R)-3-piperidinecarboxylic acid ethyl ester tartrate (4.7 g, 30 mmol) and chloroform (10 ml) was warmed to achieve dissolution. The solution was then allowed to stand for 1 week at room temperature, and was subsequently heated at reflux temperature for 7 h. After cooling, the mixture was diluted with benzene and washed with 5% ammonia. The organic phase was dried (potassium carbonate) and evaporated. The residue was purified by column chromatography on silica gel (55 g) using first benzene and then diethyl ether as eluents to give 4.1 g (53%) of (R)-1-(11H-dibenz[b,f][1,4]oxathiepin-11-ylmethyl)-3-piperidinecarboxylic acid ethyl ester as an oil.

후처리

  1. customprepared similarly
  2. dissolutiondissolution
  3. waitto stand for 1 week at room temperature
  4. temperaturewas subsequently heated
  5. temperatureat reflux temperature for 7 h
  6. temperatureAfter cooling
  7. washwashed with 5% ammonia
  8. dry with materialThe organic phase was dried (potassium carbonate)
  9. customevaporated
  10. customThe residue was purified by column chromatography on silica gel (55 g)

출처 및 근거

ORD 기록
ord-94fb46206e0d447d83b01833d2315c29
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06060468

반응 노트

불러오는 중…