Tetrabutylammonium Fluoride → HCID 58573912, compound

HRID 932254Notes

Reaction equation

HRID 932254 reaction equation
[CH2:1]([C@@:4]1([CH3:48])[CH2:9][C@H:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([Cl:17])[CH:11]=2)[C@@H:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[N:6]([C@@H:25]([CH2:45][CH3:46])[CH2:26][O:27][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[C:5]1=[O:47])[CH:2]=[CH2:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O.CCOC(C)=O>[CH2:1]([C@@:4]1([CH3:48])[CH2:9][C@H:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([Cl:17])[CH:11]=2)[C@@H:7]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[N:6]([C@@H:25]([CH2:45][CH3:46])[CH2:26][OH:27])[C:5]1=[O:47])[CH:2]=[CH2:3]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68000019HCID 68000019, compound

Product 1

HCID 58573912HCID 58573912, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3S,5R,6S)-3-allyl-1-((S)-1-((tert-butyldiphenylsilyl)oxy)butan-2-yl)-5-(3-chloro-5-fluorophenyl)-6-(4-chlorophenyl)-3-methylpiperidin-2-one (2.15 g, 3.06 mmol; Example 393, Step A) in THF (30.6 ml) at rt was added TBAF (1.0 M in THF) (6.12 ml, 6.12 mmol). The light yellow mixture was stirred at rt overnight. The mixture was diluted with water and EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (40 g column; eluent: 0 to 50% EtOAc in hexanes) to give the title compound.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by flash chromatography on silica gel (40 g column; eluent: 0 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-add2746020134e3982c4c2f46a523f5a
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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