Hydrochloric Acid → (R)-2-(4-Chloro-2-methylphenoxy)-2-(S)-pyrrolidin-3-yl-ethanol

To a solution of (S)-3-[(R)-2-benzyloxy-1-(4-chloro-2-methylphenoxy)ethyl]-pyrrolidine•TFA (4.6 mg, 10 μmol) in EtOH (2.0 mL) at room temperature, was added concentrated HCl (˜50 μL). To the stirred mixture was added 20% Pd(OH)2/C (50 wt % water, 4.0 mg). The resulting mixture was degassed and flushed with hydrogen three times and then hydrogenated under a hydrogen balloon for 25 minutes. The mixture was filtered and the filtrate was concentrated. The resulting residue was redissolved in a mixture of AcOH (0.5 mL) and water (1.0 mL), filtered and purified by reverse phase preparative HPLC to yield the title compound as a mono-TFA salt (0.6 mg, 98% purity). MS m/z: [M+H]+ calcd for C13H18ClNO2, 256.10; found 256.2.

1. customThe resulting mixture was degassed
2. customflushed with hydrogen three times
3. customfor 25 minutes
4. filtrationThe mixture was filtered
5. concentrationthe filtrate was concentrated
6. dissolutionThe resulting residue was redissolved in a mixture of AcOH (0.5 mL) and water (1.0 mL)
7. filtrationfiltered
8. custompurified by reverse phase preparative HPLC

ORD record

ord-ee9bfbc506714948abcad6378861e133

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273786B2