Sodium Bicarbonate → (3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxy-3,3-dimethylbutan-2-yl)-3-methylpiperidin-2-one

HRID 1048557Notes

Reaction equation

HRID 1048557 reaction equation
[O-]S(C(F)(F)F)(=O)=O.[CH2:9]([C@@:12]1([CH3:39])[CH2:17][C@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[C@@H:15]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[N+:14]2[C@@H:32]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:33][O:34][C:13]1=2)[CH:10]=[CH2:11].C([O-])(O)=[O:41].[Na+]>ClCCCl>[CH2:9]([C@@:12]1([CH3:39])[CH2:17][C@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[C@@H:15]([C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)[N:14]([C@@H:32]([C:35]([CH3:37])([CH3:38])[CH3:36])[CH2:33][OH:41])[C:13]1=[O:34])[CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86660745(3S,5S,6R,8S)-8-Allyl-3-(tert-butyl)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-8-methyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium triflate

Product 1

HCID 58574025(3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxy-3,3-dimethylbutan-2-yl)-3-methylpiperidin-2-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (3S,5S,6R,8S)-8-allyl-3-(tert-butyl)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-8-methyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium trifluoromethanesulfonate (290 mg, 0.478 mmol; Example 363, Step B) in 1,2-dichloroethane (4.78 mL) was added 5 mL of sat. aq. NaHCO3 solution. The reaction mixture was heated to 50° C. for 3 d. The reaction mixture was poured into a separatory funnel and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with sat. aq. NaHCO3 solution, dried over MgSO4, filtered and the filtrate was concentrated. Purification by column chromatography using 25-35% ethyl acetate in hexanes on a 4 g silica gel column afforded the title compound.

Workup

  1. additionThe reaction mixture was poured into a separatory funnel
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with sat. aq. NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-b2905d812a4a4506813c22e53d3be56c
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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