Ethanol → HCID 68826142, compound

A solution of 1 M diisobutylaluminum hydride in toluene (14.0 mL, 14.1 mmol) was slowly dropped into a cooled (−78° C.) solution of 1.6 g (5.7 mmol) of 4-methoxycarbonylmethyl-3,3-dimethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester obtained in the above 1) of PREPARATION EXAMPLE 20 in tetrahydrofuran (70 mL) under an atmosphere of argon. After dropping, the solution was stirred for 2 hours at the same temperature. After the reaction was completed, ethanol (10 mL) was added at 0° C. and the solution was 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, it was extracted with ether, and dried over anhydrous sodium sulfate. After drying, the extract was filtered and the 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 1.1 g (yield 76.4%) of 4-(2-hydroxylethyl)-3,3-dimethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester. Its physical property is shown below.

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

ORD record

ord-7263ca15bd0a461da290b2fd55b38647

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07511144B2