Water → {1-Azabicyclo[3.2.1]octan-5-yl}methanol

A cooled (0° C.) solution of 1.0N lithium aluminum hydride/tetrahydrofuran (55 mL, 55 mmol) under nitrogen was treated dropwise with a solution of 1-azabicyclo[3.2.1]octane-5-carboxylic acid ethyl ester (9.17 g, 50 mmol) in anhydrous tetrahydrofuran (20 mL), stirred for 30 minutes at room temperature, refluxed for one hour, and cooled (0° C.). In sequence, water (2.1 mL), 15% sodium hydroxide solution (2.1 mL) and water (6.3 mL) were carefully added dropwise, and the mixture was filtered through Celite (the solid was washed with tetrahydrofuran) and concentrated in vacuo to afford 6.50 g (92%) of viscous, colorless oil, which can be used as is or can be solidified on cooling; mp 44°-47° C.

1. temperaturerefluxed for one hour
2. temperaturecooled (0° C.)
3. filtrationthe mixture was filtered through Celite (the solid
4. washwas washed with tetrahydrofuran) and
5. concentrationconcentrated in vacuo
6. customto afford 6.50 g (92%) of viscous, colorless oil, which
7. temperatureon cooling

ORD record

ord-3f6f7292f4214dacbbc44e42e9963d38

Source dataset

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05244907