Diethyl Ether → HCID 59371551, compound

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (45 mg, 1.2 mmol, 5.0 equiv.) in THF (1.5 mL) was added a solution of 3-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]pyridine (115 mg, 0.24 mmol) in THF (0.5 mL). The mixture was refluxed for 1 h, then cooled to room temperature. To a flask containing 4-5 g of Na2SO4 was added with stirring 40-50 mL of Et2O followed by the cooled reaction mixture. Water was subsequently added dropwise to quench residual hydride. When no more gas was generated, the mixture was filtered, and the solid phase was washed with CH2Cl2/MeOH 4:1 (100-150 mL). Solvent removal furnished crude 3-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]-5-[(1-methyl-2(S)-azetidinyl)methoxy]pyridine (97 mg, 100%), which was used in the following step without purification.

Provenance & Evidence