Benzylamine → 9-Benzyl-9-aza-tricyclo[5.3.1.02,6]undec-3-ene

To a stirred solution of tricyclo[5.2.1.02,6]dec-3-ene-8,9-diol (Preparation 36, 6.24 g, 37.6 mmol) in dioxane (100 ml) was added sodium periodate (8.04 g, 37.6 mmol) in water (80 ml) and the reaction mixture was stirred vigorously for 45 min. The reaction mixture was extracted with ethyl acetate (4×100 ml) and the combined extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude oil (6.1 g, 37.1 mmol) was diluted with dichloroethane (400 ml) and benzylamine (3.98 g, 37.1 mmol) was added. After 3 min, sodium triacetoxyborohydride (25.23 g, 119 mmol) was added and the reaction mixture was stirred at room temperature for 18 h. Saturated sodium carbonate solution (200 ml) was added, and after 30 min, the layers were separated and the aqueous layer was washed with dichloromethane (3×50 ml). The combined organic extracts were washed with brine, filtered and concentrated. The crude yellow oil was purified by flash chromatography eluting with ethyl acetate:dichloromethane (10:90) to give the title compound as a colourless oil (6.7 g, 75%)

1. extractionThe reaction mixture was extracted with ethyl acetate (4×100 ml)
2. washthe combined extracts were washed with brine
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated in vacuo
5. additionwas added
6. waitAfter 3 min
7. stirringthe reaction mixture was stirred at room temperature for 18 h
8. waitafter 30 min
9. customthe layers were separated
10. washthe aqueous layer was washed with dichloromethane (3×50 ml)
11. washThe combined organic extracts were washed with brine
12. filtrationfiltered
13. concentrationconcentrated
14. customThe crude yellow oil was purified by flash chromatography
15. washeluting with ethyl acetate:dichloromethane (10:90)

ORDレコード

ord-805e761f161547f8804c376da3734b00

出典データセット

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07494992B2