1-Tert-butyl 3-methyl 1,2,5,6-tetrahydropyridine-1,3-dicarboxylate → HCID 22258851, compound

Temperature

0 °C

To a cold (−20° C.) solution of 1-tert-butyl 3-methyl 5,6-dihydro-1,3(2H)-pyridinedicarboxylate (700.0 mg, 2.90 mmol) in dry toluene (40 mL) was added a solution of diisobutylaluminum hydride in toluene (1.5M, 4.83 mL, 7.25 mmol) dropwise under an argon atmosphere. The reaction mixture was stirred at 0° C. for 30 min and then stirred at room temperature. The reaction was quenched by an addition of water and the stirring was continued for additional 1 hr. The precipitated aluminum salts were filtered off. The filtrate was diluted with saturated NH4Cl solution, extracted with ethyl acetate. The separated organic phase was washed with brine, dried over MgSO4, filtered and evaporated to give tert-butyl 5-(hydroxymethyl)-3,6-dihydro-1(2H)-pyridinecarboxylate, which was used for the next reaction without further purification. (580.0 mg, yield 94%)

1. stirringstirred at room temperature
2. customThe reaction was quenched by an addition of water
3. waitthe stirring was continued for additional 1 hr
4. filtrationThe precipitated aluminum salts were filtered off
5. additionThe filtrate was diluted with saturated NH4Cl solution
6. extractionextracted with ethyl acetate
7. washThe separated organic phase was washed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customevaporated

ORD record

ord-9a19baf6c26e40cea806ead1c1b5c780

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07232909B2