Hydrochloric Acid → 4-Fluoro-4-methyltetrahydrofuran-3-amine hydrochloride

A mixture of crude benzyl 4-fluoro-4-methyltetrahydrofuran-3-ylcarbamate (0.597 g, from Step 5), 10% palladium on carbon (0.200 g), 1 N hydrochloric acid (5 mL, 5.00 mmol) and methanol (20 mL) was purged with hydrogen and reacted with 40 psi hydrogen using a Parr Shaker for 2.5 h. The mixture was filtered through a celite pad and the pad rinsed with methanol. The filtrate was concentrated to give crude 4-fluoro-4-methyltetrahydrofuran-3-amine hydrochloride as a tan solid (363 mg). 1H and F NMR showed patterns consistent with the desired product, as a ca. 2:1 mixture of two diastereomers. This material was taken to the next reaction without further purification.

1. customwas purged with hydrogen
2. customreacted with 40 psi hydrogen using a Parr Shaker for 2.5 h
3. filtrationThe mixture was filtered through a celite pad
4. washthe pad rinsed with methanol
5. concentrationThe filtrate was concentrated

ORD record

ord-99d10794922a47ce96f06c883a5f162b

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987268B2