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

HRID 932236Notes

Reaction equation

HRID 932236 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].[CH2:38]([S-:40])[CH3:39].[Na+]>CN(C=O)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:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[N:14]([C@@H:32]([CH2:35][CH3:36])[CH2:33][S:40][CH2:38][CH3:39])[C:13]1=[O:34])[CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 86660740HCID 86660740, compound

Product 1

HCID 58573470(3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(ethylthio)butan-2-yl)-3-methylpiperidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °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 (86 mg, 0.15 mmol; Example 339, Step A) in DMF (0.74 ml) was added sodium ethanethiolate (38 mg, 0.45 mmol). After being stirred at 25° C. for 1.5 h, the reaction was quenched (sat. aq. NH4Cl), extracted (2×EtOAc), and washed (2× brine). The combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. Purification of the residue by chromatography on silica gel (12 g SiO2, 10% and 20% EtOAc/hex) provided the title compound as a colorless liquid.

Workup

  1. customthe reaction was quenched (sat. aq. NH4Cl)
  2. extractionextracted (2×EtOAc)
  3. washwashed (2× brine)
  4. dry with materialThe combined organic layers were dried 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, 10% and 20% EtOAc/hex)

Sources & evidence

ORD record
ord-c3494f4a5c80426084e41598706ce745
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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