Hydrochloric Acid → (1S,4R)-1,2,3,4-tetrahydro-4-(methylamino)-1-naphthalenol

Temperature

0 °C

To a solution of 1,2,3,4-tetrahydro-1,4-epoxynaphthalene (2.92 g, 20 mmol) and triethylamine (0.3 mL, 2 mmol) in 40 mL of dichloromethane at 0° C. was added 9-bromo-9-borabicyclo[3.3.1]nonane (1 M solution in tetrahydrofuran, 30 mL, 30 mmol). The reaction mixture was stirred at 0° C. for 20 minutes, and a 2 M solution of methylamine in tetrahydrofuran (40 mL) was then added, forming a white precipitate. The reaction mixture was stirred at room temperature for 16 h, poured into 100 mL of 1 M aqueous hydrochloric acid, and filtered. The filtered aqueous layer was washed with dichloromethane, basified with NaOH pellets to pH 13, and then extracted with dichloromethane. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give a gummy yellow solid. The solid was slurried in diethyl ether, filtered, washed with diethyl ether and air dried to give 2.15 g of the title compounds as white powder.

1. customforming a white precipitate
2. stirringThe reaction mixture was stirred at room temperature for 16 h
3. filtrationfiltered
4. washThe filtered aqueous layer was washed with dichloromethane
5. extractionextracted with dichloromethane
6. washThe extract was washed with brine
7. dry with materialdried over magnesium sulfate
8. customevaporated in vacuo
9. customto give a gummy yellow solid
10. filtrationfiltered
11. washwashed with diethyl ether and air
12. customdried

ORD record

ord-5e9a375b1c1b4249bd510eedeaffa8ec

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586611B2