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

HRID 932246Notes

Reaction equation

HRID 932246 reaction equation
[CH2:1]([C@@:4]1([CH3:31])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:28][CH3:29])[CH:25](O)[CH3:26])[C:5]1=O)[CH:2]=[CH2:3].[OH2:32].[C:33]1([CH3:43])[CH:38]=[CH:37][C:36]([S:39]([OH:42])(=[O:41])=[O:40])=[CH:35][CH:34]=1>C1(C)C=CC=CC=1>[CH3:43][C:33]1[CH:34]=[CH:35][C:36]([S:39]([O-:42])(=[O:41])=[O:40])=[CH:37][CH:38]=1.[CH2:1]([C@@:4]1([CH3:31])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[N+:6]2[C@@H:24]([CH2:25][CH3:26])[CH:28]([CH3:29])[O:32][C:5]1=2)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58573239(3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((3S)-2-hydroxypentan-3-yl)-3-methylpiperidin-2-one

Product 1

HCID 86660747(3S,5S,6R,8S)-8-Allyl-6-(3-chlorophenyl)-5-(4-chlorophenyl)-3-ethyl-2,8-dimethyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((3S)-2-hydroxypentan-3-yl)-3-methylpiperidin-2-one (2.25 g, 4.89 mmol; Example 151, Step C) in toluene (65 mL) was added p-toluenesulfonic acid monohydrate (930 mg, 4.89 mmol). After being heated to reflux using a Dean-Stark trap for 2.5 h, the reaction was concentrated under reduced pressure to provide the title compound as a pale yellow powder.

Workup

  1. temperatureAfter being heated
  2. temperatureto reflux
  3. customfor 2.5 h
  4. concentrationthe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d0c96be338104c14adc7496b363707f9
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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