Tetrabutylammonium Fluoride → Benzyl 3-(3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-7-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1176522Notes

Reaction equation

HRID 1176522 reaction equation
[CH3:1][C:2]1([CH3:58])[C:10]2[C:5](=[C:6]([CH2:11][O:12][CH:13]3[CH:18]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[O:37][CH3:38])=[CH:21][CH:20]=4)[CH2:17][CH2:16][N:15]([C:39]([O:41][CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[O:40])[CH2:14]3)[CH:7]=[CH:8][CH:9]=2)[N:4](COCC[Si](C)(C)C)[C:3]1=[O:57].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][C:2]1([CH3:58])[C:10]2[C:5](=[C:6]([CH2:11][O:12][CH:13]3[CH:18]([C:19]4[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[O:37][CH3:38])=[CH:23][CH:24]=4)[CH2:17][CH2:16][N:15]([C:39]([O:41][CH2:42][C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)=[O:40])[CH2:14]3)[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:57]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68504422benzyl 3-[3,3-dimethyl-2-oxo-1-(2-trimethylsilanylethoxymethyl)-2,3-dihydro-1H-indol-7-ylmethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Product 1

HCID 68498981Benzyl 3-(3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-7-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 0.690 g of benzyl 3-[3,3-dimethyl-2-oxo-1-(2-trimethylsilanylethoxymethyl)-2,3-dihydro-1H-indol-7-ylmethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 7.2 ml of tetrahydrofuran is admixed with 17.9 ml of tetrabutylammonium fluoride solution (1M in tetrahydrofuran) and stirred at reflux over 26 hours. The reaction mixture is cooled, poured onto water (100 ml) and extracted with tert-butyl methyl ether (2×100 ml). The organic phases are washed with brine (1×100 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=0.22 (1:1 EtOAc-heptane); Rt=5.89.

Workup

  1. temperatureat reflux over 26 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water (100 ml)
  4. extractionextracted with tert-butyl methyl ether (2×100 ml)
  5. washThe organic phases are washed with brine (1×100 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-34b0350e446445dcb9cda3f32c055a98
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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