Morpholine → HCID 57609695, compound

Participants

Reaction Steps

To a solution of allyl ester 76 (1.24 g, 2.47 mmol) in THF (20 mL) was added morpholine (646 mg, 7.41 mmol) and Pd(PPh3)4 (29 mg, 0.025 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 7 h and diluted with Et2O (200 mL). The organic layer was washed with 0.2 N HCl and brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography on SiO2 (15:85 acetone:CH3Cl) to give acid 77 (620 mg, 75%). Data provided for only one diastereomer: IR (neat) 1721, 1639 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.20-7.40 (m, 7H), 6.89 (d, J=8.7 Hz, 2H), 4.82 (d, J=16.5 Hz, 1H), 4.70 (d, J=16.5 Hz, 1H), 4.48 (s, 2H), 4.41-4.45 (m, 1H), 4.00-4.10 (m, 3H), 3.84 (s, 3H), 3.50-3.65 (m, 2H), 2.20-2.50 (m, 2H), 2.13 (s, 3H); LRMS (ESI) Calcd. for C24H28ClNO6 [M−H] 460, found 460.

Provenance & Evidence