Sodium hydride → HCID 22128760, compound

Temperature

50 °C

A solution of 1.08 g (4.3 mmol) of (1RS,2RS,3RS,5SR)-3-(4-chloro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octan-2-ol [J. Org. Chem. 35, 802, 1970)] in 5 ml of tetrahydrofuran was added dropwise to a suspension of 0.206 g (4.3 mmol) of sodium hydride (50% dispersion in refined oil) in 6 ml of tetrahydrofuran and the mixture was stirred at 50° C. for 60 minutes. Subsequently, the mixture was cooled to room temperature and treated with 0.95 g (4.3 mmol) of 2-bromomethylnaphthalene in 5 ml of tetrahydrofuran. After 2 hours at 50° C. the reaction solution was poured into 60 ml of ice-water and extracted three times with 25 ml of ethyl acetate. The organic phases were washed with saturated sodium chloride solution, dried over magnesium sulphate, filtered and evaporated. The residue was chromatographed on silica gel using a 95:5 mixture of methylene chloride and methanol as the eluent and yielded 1.04 g (62% of theory) of (1RS,2RS,3RS,5SR)-3-(4-chloro-phenyl)-8-methyl-2-(naphthalen-2-ylmethoxy)-8-aza-bicyclo[3.2.1]octane as a light yellow oil, Rf : 0.43 (silica gel, methylene chloride;methanol=95:5), MS: 392 (M)+.

1. temperatureSubsequently, the mixture was cooled to room temperature
2. extractionextracted three times with 25 ml of ethyl acetate
3. washThe organic phases were washed with saturated sodium chloride solution
4. dry with materialdried over magnesium sulphate
5. filtrationfiltered
6. customevaporated
7. customThe residue was chromatographed on silica gel using
8. additiona 95:5 mixture of methylene chloride and methanol as the eluent

ORD record

ord-9728a45c3ac0422b8a7379c485c1f7e8

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06051712