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 932235Notes

Reaction equation

HRID 932235 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-9e2cee1aaa1344d1ae0810aa8dc1094d
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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