Hydrochloric Acid → HCID 67402414, compound

Triethylamine (10 mL) was added to a dichloromethane (90 mL) solution of Benzyl piperidin-4-ylcarbamate (5.09 g) at 0° C. followed by the dropwise addition of methanesulfonyl chloride (which may be referred to as sbo1; 3 mL; TCI) and the resulting mixture was slowly stirred overnight with raising to room temperature. 1 N Hydrochloric acid (90 mL; WAKO) was added to the reaction mixture solution, the resulting mixture was stirred for approx. 10 minute, the resulting mixture was extracted with chloroform, the organic layer was dried, then the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Yamazen; chloroform/methanol). 200 mg of this purified compound was dissolved in THF (4 mL) and the resulting mixture was added dropwise to a THF (5 mL) solution of LDA prepared from diisopropylamine (0.2 mL; WAKO) and normal butyllithium (1.6 M, 1 mL; KANTO) at −78° C. The resulting mixture was stirred for 30 minutes followed by the dropwise addition of THF (3 mL) solution of N-fluorobenzenesulfonimide (320 mg) and the resulting mixture was slowly stirred overnight with raising to room temperature. Saturated aqueous ammonium chloride solution was added to the reaction mixture solution and the resulting mixture was extracted with ethyl acetate. The organic layer was dried, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Yamazen; chloroform/methanol). The title compound (10 mg) was obtained from this purified product according to the method described in Step c of Reference Example N-14.

1. extractionthe resulting mixture was extracted with chloroform
2. customthe organic layer was dried
3. customthe solvent was evaporated under reduced pressure
4. customthe residue was purified by silica gel column chromatography (Yamazen; chloroform/methanol)
5. dissolution200 mg of this purified compound was dissolved in THF (4 mL)
6. additionthe resulting mixture was added dropwise to a THF (5 mL) solution of LDA
7. customprepared from diisopropylamine (0.2 mL; WAKO) and normal butyllithium (1.6 M, 1 mL; KANTO) at −78° C
8. stirringThe resulting mixture was stirred for 30 minutes
9. waitthe resulting mixture was slowly stirred overnight
10. temperaturewith raising to room temperature
11. extractionthe resulting mixture was extracted with ethyl acetate
12. customThe organic layer was dried
13. customthe solvent was evaporated under reduced pressure
14. customthe residue was purified by silica gel column chromatography (Yamazen; chloroform/methanol)

ORD record

ord-31120deca279447ca645ccafd1efd74d

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299055B2