HCID 20671782, compound → HCID 86757170, compound

Participants

Reaction Steps

To a solution of [2-methyl-3(S)-(4-cyanophenyl)-isoxazolidin-5(R)-yl]acetic acid (480 mg, 1.95 mmol) in CH2Cl2 (30 ml) cooled in an ice-water bath was added a 1.6M solution of O-tert-butyl-N, N-diisopropylisourea, cat. CuCl (3.7 ml). The resulting mixture was stirred at rt for 48 hrs. After filtration, the fitrate was concentrated in EtOAc and the residue dissolved in EtOAc. The EtOAc solution was washed with brine and then dried over Na2SO4. After contration, the residue was chromatographed with a mixture of EtOAc and hexane to afford 550 mg of the product as a white solid (93%). 1H NMR (300 MHz, CDCl3) δ1.44(s, 9H), 1.98(m, 1H), 2.50(dd, 1H), 2.60(s, 3H), 2.80(dd, 1H), 2.98(dt, 1H), 3.70(t, 1H), 4.64(m, 1H), 7.50(d, 2H0, 7.66(d, 2H); MS(ESI) Calc. for (M+1)+: 303. Found: 303.

Provenance & Evidence