Benzaldehyde → HCID 18464161, compound

Participants

Reaction Steps

N-(Toluene-4-sulfonyl)sarcosyl-β-(piperidin-4-yl)-D,L-alanine methyl ester hydrochloride (180 mg, 0.402 mmol) was dissolved in MeOH (3 mL). Triethylamine (56 μL), benzaldehyde (53 mg, 0.502 mmol) and 1.0 M NaBH3CN in THF (400 μL) were added and the mixture was stirred for 5 hr. 1N HCl (3 mL) was added and the mixture was stirred for 5 minutes before diluting with saturated aqueous NaHCO3 (30 mL). The mixture was extracted with EtOAc (3×25 mL) and the combined extracts were dried (Na2SO4), filtered and evaporated in vacuo to give a residue which was purified by silica gel flash chromatography (95:5:0.5 CH2Cl2/MeOH/NH4OH) to give N-(toluene-4-sulfonyl)sarcosyl-β-(N-benzylpiperidin-4-yl)-D,L-alanine methyl ester (105 mg, 52%). The title compound was prepared via hydrolysis of the methyl ester using 0.5 N aqueous NaOH in THF/water as a very hygroscopic solid.

Provenance & Evidence