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

HRID 1107272Notes

Reaction equation

HRID 1107272 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-94fb46206e0d447d83b01833d2315c29
Source dataset
uspto-grants-2000_05
Patent number
US06060468

Reaction notes

Loading…