Tetrabutylammonium Fluoride → HCID 178515594, compound

HRID 2235272Notes

Reaction equation

HRID 2235272 reaction equation
C([SiH2][O:6][C:7](C)(C)[C@@H:8]1[CH2:13][CH2:12][C@H:11]([N:14]2[CH2:18][CH2:17][CH:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])[C:15]2=[O:28])[CH2:10][CH2:9]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:27][C:21]1[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=1[CH2:19][CH:16]1[CH2:17][CH2:18][N:14]([C@H:11]2[CH2:10][CH2:9][C@@H:8]([CH2:7][OH:6])[CH2:13][CH2:12]2)[C:15]1=[O:28]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455457HCID 178455457, compound

Product 1

HCID 178515594HCID 178515594, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 1-[cis-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-3-(2,4-dichloro-benzyl)-pyrrolidin-2-one (Preparation 37) (0.12 g, 0.25 mmol) in THF (50 mL) and add TBAF (0.50 mL, 1.0 M in THF) at room temperature under nitrogen. Stir the solution overnight. Then add water (50 mL) and extract the aqueous layer with dichloromethane (3×100 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 50-80% EtOAc-Hexane) to give 0.085 g (95%) of the title compound as a white solid: Mass spectrum (ion spray): m/z=356.2, 358.2 (M+1).

Workup

  1. extractionThen add water (50 mL) and extract the aqueous layer with dichloromethane (3×100 mL)
  2. dry with materialCombine the organic layers and dry with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify by flash column chromatography (silica gel, 50-80% EtOAc-Hexane)

Sources & evidence

ORD record
ord-96b60863cfed440a8ad2e82059891868
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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