Sodium Hydroxide → HCID 68506602, compound

HRID 1176570Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:40]=[CH:39][CH:38]=[CH:37][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH:18]2[O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:33]=2[NH:32][C:31](=O)[C:30]3([CH3:36])[CH3:35])=[CH:13][CH:12]=1.COCCO[AlH2-]OCCOC.[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:40]=[CH:39][CH:38]=[CH:37][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH:18]2[O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:33]=2[NH:32][CH2:31][C:30]3([CH3:36])[CH3:35])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 110 °C

Procedure

The solution of 0.055 g of 7-(4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidin-3-yloxymethyl)-3,3-dimethyl-1,3-dihydroindol-2-one (Example 218) and 1.0 ml of toluene is admixed with 0.072 ml of Vitride and stirred at 110° C. over 1 hour. The reaction mixture is cooled to 10° C., admixed slowly with 1M NaOH and extracted with tert-butyl methyl ether (2×30 ml). The organic phases are washed successively with 1M NaOH (30 ml), water (30 ml) and brine (30 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F).

Workup

temperatureThe reaction mixture is cooled to 10° C.
extractionextracted with tert-butyl methyl ether (2×30 ml)
washThe organic phases are washed successively with 1M NaOH (30 ml), water (30 ml) and brine (30 ml)
dry with materialdried over sodium sulphate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-b6c099b84b8140838c3d9391c74eb3b9
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842688B2

Reaction notes

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