4-Chlorobenzaldehyde → HCID 43087261, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chlorobenzaldehyde (1 eq.) in MeOH were added NaHCO3 (1.3 eq.) and (β-alanine methyl ester hydrochloride (1.2 eq.). The reaction was stirred for 15 h at 20° C. under nitrogen, then cooled to 0° C. Sodium triacetoxyborohydride (1.5 eq.) was added portionwise. The reaction was then warmed to 20° C. and stirred for 8 h. The crude was concentrated under reduced pressure then partitioned between EtOAc and a saturated aqueous solution of NaHCO3. The aqueous layer was extracted twice with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/DCM/MeOH: 50/50/0, then 0/100/0, then 0/99/1) to afford 3-(4-chloro-benzylamino)-propionic acid methyl ester.

Provenance & Evidence