Sodium Hydroxide → (S)-6-Pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydronaphthalen-2-ylamine

A solution of ((S)-6-amino-5,6,7,8-tetrahydronaphthalen-2-yl)pyrrolidin-1-yl-methanone (0.49 g) in THF (5 ml) was added dropwise to a suspension of lithium aluminum hydride (0.60 g) in THF (10 ml). The mixture was stirred at RT for one hour. Water (0.6 ml) was cautiously added dropwise, followed by sodium hydroxide solution (16%; 2 ml) and water again (2 ml). The resulting precipitate was filtered off and the filtrate was concentrated. The residue was taken up in hydrochloric acid (1N) and the solution was washed with diethyl ether. The aqueous phase was basified with concentrated sodium hydroxide solution and extracted three times with dichloromethane (DCM). The combined organic phases were dried over magnesium sulfate and concentrated. The product was thus obtained with the molecular weight of 230.36 (C15H22N2); MS (ESI): 231 (M+H+). In an analogous manner, (S)-6-(4-methoxypiperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-ylamine and (S)-6-azepan-1-ylmethyl-1,2,3,4-tetrahydronaphthalen-2-ylamine were prepared.

1. filtrationThe resulting precipitate was filtered off
2. concentrationthe filtrate was concentrated
3. washthe solution was washed with diethyl ether
4. extractionextracted three times with dichloromethane (DCM)
5. dry with materialThe combined organic phases were dried over magnesium sulfate
6. concentrationconcentrated
7. customThe product was thus obtained with the molecular weight of 230.36 (C15H22N2)

ORD record

ord-c0fa8c0deff34b8295a07eb279b0f3ca

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609731B2