Cesium fluoride → HCID 68571590, compound

HRID 1176282Notes

Reaction equation

HRID 1176282 reaction equation
Cl[C:2]1[CH:42]=[CH:41][C:5]([CH2:6][O:7][CH:8]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32][CH3:33])=[CH:16][CH:15]=3)[CH2:12][CH2:11][N:10]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:9]2)=[CH:4][C:3]=1[O:43][CH2:44][CH2:45][CH2:46][O:47][CH3:48].[F-].[Cs+].[CH:51]([Sn](CCCC)(CCCC)CCCC)=[CH2:52].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(=O)([O-])O.[Na+]>O1CCOCC1>[CH3:33][O:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:24][CH2:23][CH2:22][CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH:13]2[CH2:12][CH2:11][N:10]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:9][CH:8]2[O:7][CH2:6][C:5]2[CH:41]=[CH:42][C:2]([CH:51]=[CH2:52])=[C:3]([O:43][CH2:44][CH2:45][CH2:46][O:47][CH3:48])[CH:4]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 25953Cesium fluorideHCID 81998TributylvinyltinHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 516892Sodium BicarbonateHCID 68504735Tert-butyl 3-[4-chloro-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Product 1

HCID 68571590HCID 68571590, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The solution of 0.155 g of tert-butyl 3-[4-chloro-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate (Example 31a), 0.008 g of caesium fluoride and vinyl tributyl tin in 1.0 ml of dioxane is initially charged under argon in a Schlenk apparatus with stirring. The mixture is admixed with the solution of 0.0027 g of tris(dibenzylidenacetone)dipalladium(II) and 0.0026 g of tri-tert-butylphosphine in 0.20 ml of dioxane (prepared in a Schlenk apparatus under argon). The reaction mixture is stirred at 100° C. over 24 hours, then cooled, admixed with 1M sodium hydrogencarbonate solution (20 ml) and extracted with tert-butyl methyl ether (2×25 ml). The organic phases are washed with brine (1×5 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as an orange oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.16 (6:1 toluene-methanol); Rt=29.41 (II).

Workup

  1. stirringThe reaction mixture is stirred at 100° C. over 24 hours
  2. temperaturecooled
  3. extractionextracted with tert-butyl methyl ether (2×25 ml)
  4. washThe organic phases are washed with brine (1×5 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-3e3625d8859c460da9b83d8e035bb714
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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