Tetrahydrofuran → (3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-((S)-1-(methylthio)butan-2-yl)piperidin-2-one

HRID 1048549Notes

Reaction equation

HRID 1048549 reaction equation
[CH2:1]([C@@:4]1([CH3:35])[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]([CH2:32][CH3:33])[CH2:25][S:26][CH2:27][Si](C)(C)C)[C:5]1=[O:34])[CH:2]=[CH2:3].O1CCCC1>[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([C@@:4]1([CH3:35])[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]([C@@H:24]([CH2:32][CH3:33])[CH2:25][S:26][CH3:27])[C:5]1=[O:34])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 58573955(3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-((S)-1-(((trimethylsilyl)methyl)thio)butan-2-yl)piperidin-2-one

Product 1

HCID 67998822(3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-((S)-1-(methylthio)butan-2-yl)piperidin-2-one

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

(3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-((S)-1-(((trimethylsilyl)methyl)thio)butan-2-yl)piperidin-2-one (60 mg, 0.118 mmol, Example 301, Step A) was dissolved in a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (3.5 mL, 3.5 mmol) at room temperature. The resulting solution was stirred at ambient temperature for 16 h. After that time volatiles were removed under reduced pressure, and the residue was purified by chromatography on silica gel (4 g SiO2, 10, 20, 40% EtOAc/hexane) to provide the title compound.

Workup

  1. customAfter that time volatiles were removed under reduced pressure
  2. customthe residue was purified by chromatography on silica gel (4 g SiO2, 10, 20, 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-4f6132f3b6df4a68a86d5981f6385115
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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