Ethanaminium, N,N,N-triethyl-, fluoride (1:1) → (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-hydroxyethoxy)ethyl)piperidine-1-carboxylate

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A mixture of (R)-tert-butyl 3-((R)-1-(2-(tert-butyldimethylsilyloxy)ethoxy)-1-(3-chlorophenyl)ethyl)piperidine-1-carboxylate, tetraethylammonium fluoride (7.600 g, 50.9 mmol) in CH3CN was heated at 45° C. for 1 h and then was allowed to stir at rt overnight. The reaction mixture was evaporated under reduced pressure, the residue was dissolved into water and extracted with Et2O (3×), dried over Na2SO4. After the solvent was removed in vacuo, the crude product was purified by reversed-phase HPLC to give 1.000 g (35% in two steps) of (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-hydroxyethoxy)ethyl)piperidine-1-carboxylate. MS ESI +ve m/z 406 (M+Na).

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