Acetic Acid → HCID 58266617, compound

Temperature

60 °C

To a suspension of 2-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (1.86 g, 8.50 mmol) in THF (30.6 mL) was added acetic acid (17 mL) then the reaction temperature was reduced to 0° C. and sodium borohydride (2.55 g, 42.5 mmol) was added in portions. After the addition was complete, the reaction mixture was heated at 60° C. for 1 h then the reaction mixture was cooled to ambient temperature and quenched by the addition of water. The resultant solution was partitioned between ethyl acetate (75 mL) and 1N sodium hydroxide solution (50 mL) and the layers separated. The organic phase was collected then dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to give the title compound (1.87 g, 89%). 1H NMR (MeOD, 300 MHz): 6.78 (s, 1H), 3.50 (s, 2H), 2.81 (s, 4H), 2.62 (q, J=7.2 Hz, 2H), 1.17 (t, J=7.2 Hz, 3H).

1. customwas reduced to 0° C.
2. additionAfter the addition
3. temperaturethe reaction mixture was cooled to ambient temperature
4. customquenched by the addition of water
5. customThe resultant solution was partitioned between ethyl acetate (75 mL) and 1N sodium hydroxide solution (50 mL)
6. customthe layers separated
7. customThe organic phase was collected
8. dry with materialthen dried over anhydrous sodium sulfate
9. filtrationfiltered
10. customevaporated in vacuo

ORD record

ord-41907f854f2c4f998d7111e7399423d8

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501765B2