Water → 3-Benzo[1,3]dioxol-5-yl-1-[(S)-1-(2,3-dihydrobenzo[1,4]dioxin-2-yl)methyl]-piperidine

(3-Benzo[1,3]dioxol-5-ylpiperidin-1-yl-(R)-2,3-dihydrobenzo[1,4]dioxin-2-ylmethanone (285 mg, 0.77 mmol) was dissolved in dry DMF (2.5 ml) and 1 M BH3 THF (3.10 ml, 3.10 mmol) was slowly added under a nitrogen atmosphere. The reaction mixture was stirred for 4.5 h at RT and then cooled to 0° C. Water was slowly added and the mixture basified with 2.5 M NaOH and extracted three times with EtOAc. The combined organic phases were dried (Na2SO4), filtered and evaporated to dryness. The crude product was dissolved in methanol (25 ml) and 5 M HCl (1.5 ml) was slowly added. The mixture was stirred for 1 h at RT and then at 60° C. for 2 h. The reaction mixture was evaporated to dryness, redissolved in EtOAc and washed twice with 1 M Na2CO3 and water. The combined organic phases were dried (Na2SO4), filtered and evaporated to dryness to give 228 mg of the title compound.

1. temperaturecooled to 0° C
2. extractionextracted three times with EtOAc
3. dry with materialThe combined organic phases were dried (Na2SO4)
4. filtrationfiltered
5. customevaporated to dryness
6. dissolutionThe crude product was dissolved in methanol (25 ml)
7. addition5 M HCl (1.5 ml) was slowly added
8. stirringThe mixture was stirred for 1 h at RT
9. waitat 60° C. for 2 h
10. customThe reaction mixture was evaporated to dryness
11. dissolutionredissolved in EtOAc
12. washwashed twice with 1 M Na2CO3 and water
13. dry with materialThe combined organic phases were dried (Na2SO4)
14. filtrationfiltered
15. customevaporated to dryness

ORD-Eintrag

ord-9d5536c885f54277973dcf096868dcd3

Quelldatensatz

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08697723B2