Diiodomethane → Ammonium Acetate

Participants

Reaction Conditions

Reaction Steps

A 20 mL vial was charged with 1 mL of CH2Cl2 and dimethoxyethane (78 μL, 0.75 mmol). The solution was cooled to −10° C. and diethylzinc (89 mg, 0.72 mmol) was added. To this solution was added diiodomethane (402 mg, 1.5 mmol) dropwise. After the addition was complete, the resulting clear solution was stirred for 10 minutes at −10° C. then a solution of Example 221C (65 mg, 0.19 mmol) in CH2Cl2 (0.5 mL) was added. The reaction mixture was stirred overnight at room temperature then quenched with water, and extracted with CH2Cl2. The organic extract was dried (Na2SO4), filtered and concentrated. Purification by preparative high pressure liquid chromotography on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile:ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/minutes afforded the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 0.82 (t, J=6.71, 4.58 Hz, 2H) 0.91 (t, J=5.80, 5.19 Hz, 2H) 1.41 (s, 3H) 1.60-1.67 (m, 4H) 1.81-1.88 (m, 2H) 1.90 (dd, J=10.68, 2.75 Hz, 2H) 2.16 (dd, J=10.37, 0.92 Hz, 2H) 2.29-2.36 (m, 2H) 2.72 (t, J=6.71 Hz, 1H) 3.36 (s, 3H) 3.74 (t, J=4.88 Hz, 2H) 4.41 (t, J=4.88 Hz, 2H) 6.88 (s, 1H); MS (ESI) m/z 361 (M+H)+.

Provenance & Evidence