Tetrahydrofuran → HCID 68427102, compound

HRID 2265155Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH3:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH:15]([C:26](OC)=[O:27])[CH2:14]1.[OH-].[Na+]>C(OCC)(=O)C.O>[CH3:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH:15]([CH2:26][OH:27])[CH2:14]1

Participants

Conditions

Temperature: 0 °C

Procedure

In a nitrogen atmosphere, 152 mg of lithiumaluminium hydride was added to tetrahydrofuran (20 mL) solution of 500 mg of methyl (3RS,4SR)-1-methyl-4-o-tolylpiperidine-3-carboxylate obtained in Production Example 31-1, at 0° C., and stirred at 0° C. for 30 minutes. 0.15 mL of water, 0.15 mL of aqueous 15% sodium hydroxide solution and 0.46 mL of water were added to the reaction liquid in that order, and stirred at room temperature for 1 hour. This was diluted with ethyl acetate, and dried with anhydrous sodium sulfate, and the insoluble substance was removed through filtration through Celite. The filtrate was distilled under reduced pressure, and the residue was separated and purified through silica gel column chromatography (chloroform/methanol=70/30) to obtain 470 mg of the entitled compound as a pale yellow oily substance.

Workup

customobtained in Production Example 31-1, at 0° C.
stirringstirred at room temperature for 1 hour
dry with materialdried with anhydrous sodium sulfate
customthe insoluble substance was removed through filtration through Celite
distillationThe filtrate was distilled under reduced pressure
customthe residue was separated
custompurified through silica gel column chromatography (chloroform/methanol=70/30)

Sources & evidence

ORD record: ord-f93b1d069eb944e1b3ee937f5e822f9f
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855294B2

Reaction notes

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