Hexane → HCID 9924117, compound

HRID 900777Notes

Reaction equation

HRID 900777 reaction equation
[Li]CCCC.CCCCCC.[C:12]([C:14]1([F:22])[CH:19]2[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]2)[CH2:15]1)#[CH:13].[CH:23]1([C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C1COCC1>[CH:31]1([C:29]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([OH:30])[C:13]#[C:12][C:14]2([F:22])[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 12837Cyclohexyl phenyl ketoneHCID 9964153HCID 9964153, compoundHCID 178418339Butyllithium

Product 1

HCID 9924117HCID 9924117, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.6 N solution of BuLi in hexane (730 μA, 1.16 mmol) was added dropwise to a solution of 3-ethynyl-3-fluoroquinuclidine 57 (162 mg, 1.06 mmol) in THF (5 ml) at 0° C. After stirring for 30 minutes, cyclohexyl(phenyl)methanone (207 mg, 1.16 mmol) in THF (1 ml) was added slowly. After 30 minutes, the reaction was quenched by the addition of saturated aqueous NH4Cl solution and diluted with AcOEt. The organic phase was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by chromatography over silica gel (CH2Cl2/MeOH 97.5/2.5) and 1-cyclohexyl-3-(3-fluoro-1-azabicyclo[2.2.2]oct-3-yl)-1-phenylprop-2-yn-1-ol 111 was obtained as colorless foam (mixture of diastereomers, 30 mg, 8%).

Workup

  1. waitAfter 30 minutes
  2. customthe reaction was quenched by the addition of saturated aqueous NH4Cl solution
  3. additiondiluted with AcOEt
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by chromatography over silica gel (CH2Cl2/MeOH 97.5/2.5)

Sources & evidence

ORD record
ord-b3311eca39eb4b0d9289abcbad340c58
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

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