Ethanol → tert-Butyl 3-[4-furan-2-yl-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1176369Notes

Reaction equation

HRID 1176369 reaction equation
Br[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].[CH2:49](O)[CH3:50].[C:52](=[O:55])([O-])[O-].[Na+].[Na+].[C:58](=O)([O-])O.[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:55]1[CH:52]=[CH:50][CH:49]=[C:58]1[C:2]1[CH:42]=[CH:41][C:5]([CH2:6][O:7][CH:8]2[CH:13]([C:14]3[CH:15]=[CH:16][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:18][CH:19]=3)[CH2:12][CH2:11][N:10]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:9]2)=[CH:4][C:3]=1[O:43][CH2:44][CH2:45][CH2:46][O:47][CH3:48]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 68501394Tert-butyl 3-[4-bromo-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Product 1

HCID 68505883tert-Butyl 3-[4-furan-2-yl-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The mixture of 0.500 g of tert-butyl 3-[4-bromo-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate and 0.023 g of tetrakis(triphenylphosphine)palladium(0) in 6.0 ml of 1,2-dimethoxyethane is stirred at room temperature over 10 minutes, then admixed with 0.114 g of 2-furanboric acid, 0.70 ml of ethanol and 0.68 ml of 2M sodium carbonate solution and stirred at 80° C. over 16 hours. The reaction mixture is cooled, poured onto 1M sodium hydrogencarbonate solution (40 ml) and extracted with tert-butyl methyl ether (2×40 ml). The organic phases are washed successively with water (40 ml) and brine (40 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a brown oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.43 (1:1 EtOAc-heptane); Rt=6.32.

Workup

  1. stirringstirred at 80° C. over 16 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with tert-butyl methyl ether (2×40 ml)
  4. washThe organic phases are washed successively with water (40 ml) and brine (40 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1806d30f2e00481cb38dceb76e671e7e
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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