Methanol → 4-Aminobicyclo[2.2.1]heptan-1-ol hydrochloride

A 2-L Parr bottle was charged with benzyl 4-hydroxybicyclo[2.2.1]heptan-1-ylcarbamate (61 g, 233 mmol), methanol (400 mL), and water (200 mL). The Parr bottle was flushed with nitrogen and charged with 10% palladium on carbon (25 g, 11.65 mmol, 50% wet with water). The reaction was run under 30 gpsi hydrogen on a parr shaker for 3 h when TLC analysis (15% methanol/DCM with 2% ammonium hydroxide) indicated a complete reaction. The reaction was filtered through a celite plug and concentrated to remove methanol. The resulting aqueous mixture was treated with 2 N hydrochloric acid (115 mL) until it reached pH 1-2. The aqueous mixture was extracted using ethyl acetate (5×400 mL) to remove an impurity. The aqueous mixture was concentrated to dryness and dried in a vacuum oven at 40° C. overnight to provide 36.91 g (97%) of 4-aminobicyclo[2.2.1]heptan-1-ol hydrochloride; MS (ESI) m/z 128.1 [M+1]+

1. customThe Parr bottle was flushed with nitrogen
2. customa complete reaction
3. filtrationThe reaction was filtered through a celite plug
4. concentrationconcentrated
5. customto remove methanol
6. additionThe resulting aqueous mixture was treated with 2 N hydrochloric acid (115 mL) until it
7. extractionThe aqueous mixture was extracted
8. customto remove an impurity
9. concentrationThe aqueous mixture was concentrated to dryness
10. customdried in a vacuum oven at 40° C. overnight

ORD record

ord-75d89ddf03894c8ab8de90b029b179cd

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139534B2