Hydrochloric Acid → (2-{5-[2-(5-Fluoro-2-methoxy-phenyl)-ethyl]-tetrahydro-furan-2-yl}-ethyl)-methyl-amine

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Reaction Steps

In a flame dried round bottom flask, purged with Ar(g), was placed 19 (112 mg, 0.33 mmol, 1.0 eq) and anhydrous THF (1.6 mL). The flask was then cooled with an ice bath while stirring for 15 min. LAH (1.0 M, 1.32 mL, 1.32 mmol, 4.0 eq) was then slowly added via a syringe over a period of 5 min. The reaction was allowed to warm to rt and stirred an additional 4 hrs. The reaction was then stopped by addition of ice cold MeOH and then stirred at rt for an additional 15 min. The resulting solution was transferred to a beaker with the aid of 1N HCl(aq) and then made basic with 10 M NaOH(aq). The basic solution was then extracted with Et2O (3×20 mL) and the organic layer was washed with brine. The Et2O layer was dried over Mg2SO4 for 15 min and filtered through paper and concentrated to an oil under reduced pressure to afford the crude product. The oil was purified with PTLC and eluted with MeOH:CH2Cl2 (5:95). (Rf=0.05, Methanol/DCM, 5:95, v:v); 1H NMR (CDCl3, 500 MHz) 6.87-6.82 (m, 2 H), 6.74-6.71 (m, 1 H), 4.05-3.77 (m, 2 H), 3.78 (s, 3 H), 2.71-2.56 (m, 5 H), 2.08-1.51 (m, 10 H); HRMS (ESI) [M+H]+ calcd for C16H25FNO2 282.3784, found 282.3762; HPLC>97% (tR=30.23 min, 100(A):0.5(D); tR=26.05 min, 90(A):10(C):0.5(D)).

Provenance & Evidence