Water → HCID 22492926, compound

To a solution of 1-N-t-butyloxycarbonyl-4-hydroxypiperidine (5.0 g) in dimethylformamide (DMF) (25 ml) was portionwise added sodium hydride (60% in oil) (1.29 g) with stirring under ice-cooling. The mixture was successively stirred at ambient temperature for 30 minutes, stirred at 60° C. for 1 hour and cooled with an ice bath. To the reaction mixture was added 1,5-dibromopentane (6.72 ml), and the mixture was stirred at ambient temperature for 3 hours. The reaction solution was poured into water (100 ml) and extracted twice with a mixture of ethyl acetate (80 ml) and n-hexane (30 ml). The extract was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (200 ml) eluting with a mixture of n-hexane and ethyl acetate (5:1 v/v). The fractions containing the desired compound were collected and evaporated under reduced pressure to give 4-(5-bromopentyloxy)-1-N-t-butyloxycarbonylpiperidine (2.44 g).

1. temperaturecooling
2. stirringThe mixture was successively stirred at ambient temperature for 30 minutes
3. stirringstirred at 60° C. for 1 hour
4. temperaturecooled with an ice bath
5. stirringthe mixture was stirred at ambient temperature for 3 hours
6. extractionextracted twice with a mixture of ethyl acetate (80 ml) and n-hexane (30 ml)
7. washThe extract was washed with saturated aqueous sodium chloride
8. dry with materialdried over magnesium sulfate
9. customevaporated in vacuo
10. customThe resulting residue was chromatographed on silica gel (200 ml)
11. washeluting with a mixture of n-hexane and ethyl acetate (5:1 v/v)
12. additionThe fractions containing the desired compound
13. customwere collected
14. customevaporated under reduced pressure

ORD record

ord-9e6e8679af7943b98628786839dad7ee

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06884868B1