Sodium cyclopropanesulfinate → (3S,5R,6S)-3Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(cyclopropylsulfonyl)butan-2-yl)-3-methylpiperidin-2-one

HRID 1048551Notes

Reaction equation

HRID 1048551 reaction equation
FC(F)(F)S([O-])(=O)=O.[CH2:9]([C@@:12]1([CH3:37])[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]([CH2:35][CH3:36])[CH2:33][O:34][C:13]1=2)[CH:10]=[CH2:11].[Na+].[CH:39]1([S:42]([O-:44])=[O:43])[CH2:41][CH2:40]1>C(#N)C>[CH2:9]([C@@:12]1([CH3:37])[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]([CH2:35][CH3:36])[CH2:33][S:42]([CH:39]2[CH2:41][CH2:40]2)(=[O:44])=[O:43])[C:13]1=[O:34])[CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 42643363Sodium cyclopropanesulfinateHCID 86660740(3S,5S,6R,8S)-8-allyl-6-(3-chlorophenyl)-5-(4-chlorophenyl)-3-ethyl-8-methyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium trifluoromethanesulfonate

Product 1

HCID 58573516(3S,5R,6S)-3Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(cyclopropylsulfonyl)butan-2-yl)-3-methylpiperidin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (3S,5S,6R,8S)-8-allyl-6-(3-chlorophenyl)-5-(4-chlorophenyl)-3-ethyl-8-methyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium trifluoromethanesulfonate (75 mg, 0.130 mmol; Example 339, Step A) in acetonitrile (1.3 mL) was added cyclopropanesulfinic acid sodium salt (50 mg, 0.39 mmol) at 25° C. After being stirred at 90° C. for 1 day, the reaction was quenched with sat. aq. NH4Cl solution, extracted (2×EtOAc) and the combined organic layers wer washed with brine (2×), dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. Purification of the residue by chromatography on silica gel (12 g SiO2, 35% and 45% EtOAc/hex) provided the title compound as a colorless liquid.

Workup

  1. customthe reaction was quenched with sat. aq. NH4Cl solution
  2. extractionextracted (2×EtOAc)
  3. washthe combined organic layers wer washed with brine (2×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customPurification of the residue by chromatography on silica gel (12 g SiO2, 35% and 45% EtOAc/hex)

Sources & evidence

ORD record
ord-0df22a8ee64b43d8b7c89f2fe5ffdbbb
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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