p-Toluenesulfonic acid monohydrate → (3S,5S,6R,8S)-8-Allyl-5-(4-chloro-3-fluorophenyl)-6-(3-chlorophenyl)-3-cyclopropyl-8-methyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium 4-methylbenzenesulfonate

HRID 1846978Notes

Reaction equation

HRID 1846978 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:13]([C@@:16]1([CH3:44])[CH2:21][C@H:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[C@@H:19]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([F:36])[CH:30]=2)[N:18]([C@@H:37]([CH:40]2[CH2:42][CH2:41]2)[CH2:38][OH:39])[C:17]1=O)[CH:14]=[CH2:15]>C1(C)C=CC=CC=1>[CH3:12][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O-:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH2:13]([C@@:16]1([CH3:44])[CH2:21][C@H:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[C@@H:19]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([F:36])[CH:30]=2)[N+:18]2[C@@H:37]([CH:40]3[CH2:42][CH2:41]3)[CH2:38][O:39][C:17]1=2)[CH:14]=[CH2:15]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86731826(3S,5R,6S)-3-Allyl-6-(4-chloro-3-fluorophenyl)-5-(3-chlorophenyl)-1-((S)-1-cyclopropyl-2-hydroxyethyl)-3-methylpiperidin-2-one

Product 1

HCID 86731827(3S,5S,6R,8S)-8-Allyl-5-(4-chloro-3-fluorophenyl)-6-(3-chlorophenyl)-3-cyclopropyl-8-methyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

p-Toluenesulfonic acid monohydrate (30.3 g, 159 mmol, Aldrich, St. Louis, Mo.) was added to a solution of (3S,5R,6S)-3-allyl-6-(4-chloro-3-fluorophenyl)-5-(3-chlorophenyl)-1-((S)-1-cyclopropyl-2-hydroxyethyl)-3-methylpiperidin-2-one (73.6 g, 154 mmol) in toluene (386 mL). The reaction mixture was heated at reflux using a Dean-Stark apparatus. After 4 hours, the reaction was cooled and concentrated under reduced pressure to provide the title compound as a pale yellow syrup. The crude product was used in next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux
  3. temperaturethe reaction was cooled
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fadde94b5eeb4aa5b42a742232527327
Source dataset
uspto-grants-2015_02
Patent number
US08952036B2

Reaction notes

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