Sodium Hydroxide → 1'-Methylspiro[indoline-3,4'-piperidine]

HRID 2265147Notes

Reaction equation

[Na].[H-].COCCO[Al+]OCCOC.C1(C)C=CC=CC=1.CS([N:25]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:27]2([CH2:32][CH2:31][N:30]([C:33](OCC3C=CC=CC=3)=O)[CH2:29][CH2:28]2)[CH2:26]1)(=O)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:33][N:30]1[CH2:29][CH2:28][C:27]2([C:43]3[C:48](=[CH:47][CH:46]=[CH:45][CH:44]=3)[NH:25][CH2:26]2)[CH2:32][CH2:31]1

Participants

Conditions

Temperature: 0 °C

Procedure

In a nitrogen atmosphere, 3.8 mL of 65% sodium-bis(2-methoxyethoxy)aluminium hydride-toluene solution was added to toluene (20 mL) solution of 1 g of benzyl 1-methanesulfonyl-spiro[2,3-dihydro-1H-indole-3,4′-piperidine]-1′-carboxylate (prepared according to the method described in Tetrahedron, 1997, 53, 10983-10992), and refluxed for 3 hours. The reaction liquid was cooled to 0° C., poured into aqueous 1 M sodium hydroxide solution at that temperature, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through silica gel column chromatography (aqueous 1% ammonia, chloroform/methanol=5/1) to obtain 0.32 g of the entitled compound.

Workup

customprepared
temperaturerefluxed for 3 hours
customThe reaction liquid
extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated saline water
dry with materialdried with anhydrous magnesium sulfate
customThe solvent was evaporated off under reduced pressure
customthe residue was separated
custompurified through silica gel column chromatography (aqueous 1% ammonia, chloroform/methanol=5/1)

Sources & evidence

ORD record: ord-6b2ebfe7853b4e7fb59126496cca2c85
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855294B2

Reaction notes

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