Sodium borohydride → HCID 58675134, compound

Participants

Reaction Steps

Sodium borohydride (198 mg, 5.20 mmol) was added in one portion to a stirred solution of 5-(4-iodo-phenyl)-3-oxo-pentanoic acid tert-butyl ester (Intermediate 8, 1.78 g, 4.76 mmol) in methanol (15 mL) at 0° C. The reaction was stirred for 20 minutes then quenched with 1 M HCl (15 mL). The resulting mixture was extracted with diethyl ether (3×20 mL). The organic phases were combined, dried (MgSO4) then the solvent removed by evaporation under reduced pressure to give the title compound (1.46 g, 82%) as a colourless oil. LC/MS: 3.59 min; z/e 394, calcd (M+NH4) 394. 1H NMR (400 MHz: CDCl3): 7.6 (2 H), 6.95 (2 H), 3.95 (1 H), 2.7 (2 H), 2.38 (2 H), 1.73 (2 H), 1.45 (9 H).

Provenance & Evidence