1-(Phenyl(tetrahydrofuran-2-yl)methyl)urea → 1-((S)-phenyl((S)-tetrahydrofuran-2-yl)methyl)urea

Participants

Reaction Steps

The enantiomers of 1-(phenyl(tetrahydrofuran-2-yl)methyl)urea (150 mg, 0.681 mmol) were separated by SFC (Berger Multigram II, Column: Chiral Technology OZ-H 2.1×25 cm, SuM, UV wavelength: 220 nM, mobile phase: 40%/60% Methanol+0.25% dimethyl ethylamine/CO2(1), flow rate: 70 mL/Min, 7 min run time). Elution was observed at 2.46 min. The fractions were collected and the solvent evaporated in vacuo to afford 1-((S)-phenyl((S)-tetrahydrofuran-2-yl)methyl)urea and Intermediates 149A-151A. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 7.23 (m, 4H), 7.18 (m, 1H), 6.43 (d, J=9.5, 1H), 5.57 (br s, 2H), 4.68-4.47 (dd, J=3.5, J=5.5, 1H), 3.97 (m, 1H), 3.76 (q, J=8.0 1H), 3.56 (q, J=7.0, 1H), 1.79-1.75 (m, 3H), 1.73 (m, 1H).

Provenance & Evidence