Ethanol → HCID 68824202, compound

Into a cooled (−78° C.) solution of 4-methoxycarbonylmethylene-3,3-dimethylpiperidine-1-carboxylic acid t-butyl ester (1.8 g, 6.4 mmol) in tetrahydrofuran (50 mL) obtained in the above 1) was slowly dropped, under an atmosphere of argon, 1 M diisobutylaluminum hydride in toluene (15.9 mL, 15.9 mmol). After dropping, the reaction mixture was stirred for 2 hours at the same temperature. After the reaction was completed, ethanol (10 mL) was added at 0° C. and allowed to warm to room temperature gradually. The reaction mixture was then concentrated under a reduced pressure, treated with an aqueous solution of 20% sodium potassium tartrate (50 mL), and stirred for 30 minutes. After stirring, the reaction mixture was extracted with ether, and dried over anhydrous sodium sulfate. After drying, the extract was filtered and filtrate was concentrated under a reduced pressure. The residue was subjected to silica gel column chromatography (developing solvent, hexane:ethyl acetate=2: 1) to obtain 0.95 g (yield 58.6%) of 4-(2-hydroxyethylidene)-3,3-dimethylpiperidine-1-carboxylic acid t-butyl ester. Its physical property is shown below.

1. customobtained in the above 1)
2. additionwas slowly dropped, under an atmosphere of argon
3. concentrationThe reaction mixture was then concentrated under a reduced pressure
4. additiontreated with an aqueous solution of 20% sodium potassium tartrate (50 mL)
5. stirringstirred for 30 minutes
6. stirringAfter stirring
7. extractionthe reaction mixture was extracted with ether
8. dry with materialdried over anhydrous sodium sulfate
9. customAfter drying
10. filtrationthe extract was filtered
11. concentrationfiltrate was concentrated under a reduced pressure

ORD record

ord-5186bd1ffcc24a888a0bb47a8e2cf0c2

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07511144B2