Thiophene → HCID 58032833, compound

Temperature

-78 °C

A 1.6 M solution of n-BuLi in Hex (3.71 ml, 5.9 mmol) was added to a cooled (−78° C.) solution of thiophene (500 mg, 5.9 mmol) in THF (15 ml) under Ar. After stirring 30 min at −78° C. a solution of N-fluorodibenzenesulfonimide (1.87 g, 5.9 mmol) in THF (10 ml) was added. Stirring at −78° C. was continued for 10 min before slow rising of the temperature to 0° C. over a period of 15 min. A solid precipitate was formed. The mixture was cooled to −78° C., a 1.6 M n-BuLi solution in Hex (3.71 ml, 0.59 ml) was added, then it was stirred 10 min before addition of 4-formyl-piperidine-1-carboxylic acid tert-butyl ester (836 mg, 3.9 mmol) in THF (5 ml). After stirring 30 min at −78° C. the solution was slowly warmed to room temperature. Sat. aq. NH4Cl sol. (5 ml) was added, the mixture was diluted with EtOAc (100 ml) and washed with sat. aq. NH4Cl sol. (100 ml), sat. aq. NaHCO3 (2×100 ml) and brine (100 ml). After drying (Na2SO4) and evaporation of the solvent, the crude product was purified by chromatography (amino modified silica gel, Hept to EtOAc) to yield 971 mg (79%) of a brown oil. MS (m/z): 316.1 ([M+H]+).

1. additionwas added
2. customA solid precipitate was formed
3. temperatureThe mixture was cooled to −78° C.
4. stirringAfter stirring 30 min at −78° C. the solution
5. temperaturewas slowly warmed to room temperature
6. washwashed with sat. aq. NH4Cl sol. (100 ml), sat. aq. NaHCO3 (2×100 ml) and brine (100 ml)
7. customAfter drying
8. custom(Na2SO4) and evaporation of the solvent
9. customthe crude product was purified by chromatography (amino modified silica gel, Hept to EtOAc)

ORD record

ord-6afad31991324bf6ac1f5d6ee1251840

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415350B2