Sodium Sulfite → (2R)-5-Phenyl-2-methylpentanoic acid

Participants

Reaction Conditions

Reaction Steps

(4S)-3-((2R)-5-Phenyl-2-methyl-1 -oxopentyl)-4-isopropyl-1,3-oxazolidin -2-one (0.25 g, 0.83 mmol), prepared by the method described in J. Org. Chem. 59: 2261, (1994), was dissolved in 4.2 mL of 4:1 THF:H2O, cooled to 0° C. and purged with N2. 30% Hydrogen peroxide (0.34 mL) was added dropwise, followed by a dropwise addition of a solution of LiOH·H2O (31.9 mg, 1.3 mmol) and 1.7 mL H2O. The reaction mixture was stirred at 0° C. for 1 hour, then a solution of sodium sulfite (0.42 g, 3.3 mmol) in 2.5 mL of H2O was added. THF was evaporated in vacuo, and H2O was added to the residue. This mixture was washed with CH2Cl2 (3×). The aqueous layer was cooled to 0° C., acidified with aqueous hydrochloric acid and extracted (5×) with EtOAc. The combined EtOAc extracts were dried (MgSO4), filtered, and concentrated in vacuo to afford the title compound (0.11 g) as a colorless oil. 1HNMR (300 MHz, CDCl3) δ 1.18 (d, 3H), 1.50 (m, 3H), 1.60-1.80 (m, 3H), 2.5 (m, 1H), 2.62 (t, 2H), 7.08 (m, 3H), 7.29 (m, 2H). MS (DCl/NH3) m/e 210 (M+NH4)+.

Provenance & Evidence