Hydrogen Peroxide → HCID 86705568, compound

Participants

Reaction Conditions

Reaction Steps

To a 1M LiOH solution (8.20 mL, 8.20 mmol) cooled to 0° C. was added 30% hydrogen peroxide (1.06 mL, 10.2 mmol). The mixture was stirred for 10 min at 0° C. and then added to solution of 340 (2.10 g, 4.10 mmol) in THF (15 mL) cooled to 0° C. over 15 min. The mixture was stirred for 4 h at 0° C. then 2M sodium sulfite (10 mL) was added and the mixture stirred for 30 min. The pH was adjusted to ca. 5-6 with 2M KHSO4 and the mixture was thrice extracted with 50 mL portions of 3:1 CHCl3/IPA. The combined organic extracts were combined, washed with brine, dried (MgSO4), filtered and evaporated. The crude product was purified by SiO2 chromatography eluting with a MeOH/DCM gradient (5 to 10% MeOH) to afford 1.28 g (85.0%) of (3S,4R)-1-benzyl-4-(3-fluoro-4-(trifluoromethyl)phenyl)pyrrolidine-3-carboxylic acid (342) as white solid: MS m/z (APCI-neg) M−1=366.

Provenance & Evidence