Diisopropylethylamine → HCID 123477066, compound

Participants

Reaction Steps

To a solution containing the product from Example 2C (0.020 g, 0.038 mmol) in tetrahydrofuran (0.40 mL) were added the product from Example 156C (0.008 g, 0.041 mmol), DEPBT (0.015 g, 0.050 mmol), and N,N-diisopropylethylamine (0.020 mL, 0.115 mmol) and the mixture was stirred at room temperature for 1 hour. The mixture was partitioned between ethyl acetate and 10% Na2CO3 solution. The organic was washed with additional 10% Na2CO3 solution and then brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel eluting with a gradient starting with dichloromethane and ending with 50% acetone in dichloromethane to give the product (0.015 g, 56% yield). 1H NMR (300 MHz, DMSO-d6), δ ppm 0.81 (s, 9 H), 0.97 (s, 3 H), 1.01 (s, 3 H), 1.49-1.53 (m, 2 H), 2.53-2.60 (m, 1 H), 2.76-2.81 (m, 3 H), 2.93 (s, 3 H), 3.49 (s, 3 H), 3.64-3.70 (m, 1 H), 3.83 (d, J=9.9 Hz, 1 H), 4.21 (d, J=6.3 Hz, 1 H), 4.17-4.30 (m, 2 H), 4.98 (d, J=5.5 Hz, 1 H), 6.28 (d, J=6.3 Hz, 1 H), 6.67 (d, J=9.92 Hz, 1 H), 7.12-7.33 (m, 9 H), 7.52 (d, J=9.6 Hz, 1 H), 7.80-7.91 (m, 5 H), 8.64 (d, J=4.8 Hz, 1 H).

Provenance & Evidence