Acetic Acid → (2S,3R)-3-amino-1-[[3-(4-fluorophenyl)propyl](2,2,2-trifluoroethyl)amino]butan-2-ol

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Reaction Steps

Pd(OH)2 was carefully wetted down under N2 with 20 mL of MeOH and the product of Step d (3.78 g) dissolved in 50 mL of MeOH was added followed by 70 mL of HOAc. The mixture was hydrogenated for 3 days on a Parr shaker at 50 PSI. Worked up by filtering off the catalyst under N2 and vacuum through a fiberglass filter paper to obtain an oil. To the oil was added Et2O/saturated NaHCO3 (100 mL) The layers were separated. The aqueous was basified further with 1N NaOH to pH=12 then extracted 3 times with Et2O. The Et2O extracts from the 1N NaOH layer were combined, dried (Na2SO4) and stripped to give 2.46 g of and amber oil. The oil was purified by flash chromatography in 9:1 Hexanes/EtOAc to 100% EtOAc. Obtained 192 mg of an oil. MS (ESI) detects (M+H)+=323.

Provenance & Evidence