Sodium Iodide → HCID 54314874, compound

Participants

Reaction Steps

A solution of 900 mg (6.0 mmol) of 3-(R)-phenylbutan-1-ol (from EXAMPLE 104, Step A) and 3.0 mL (18.0 mmol) of DIEA in 10 mL of CH2Cl2 was treated with 0.7 mL (9.0 mmol) of methanesulfonyl chloride and the resulting mixture was stirred at rt for 1 h. The reaction was quenched with H2O and 50 mL of 1.0 N HCl. The quenched mixture was extracted 3× with CH2Cl2. The organic extracts were washed with sat'd NaCl, dried over Na2SO4, filtered and the filtrate concentrated. A mixture of the residue and 9.0 g (60.0 mmol) of NaI in 10 mL of acetone was heated at reflux for 2 h. The reaction mixture cooled and concentrated. The residue was diluted with H2O and extracted 3× with CH2Cl2. The extracts were washed with sat'd NaCl, dried over Na2SO4, filtered and the filtrate concentrated. The residue was purified by flash chomatography on 50 g of silica eluting with 0-20% EtOAc/hexanes (v/v) to give 1.4 g (90%) of the title compound: 1H NMR (500 MHz) δ 1.31 (d, J=6.9, 31), 2.10-2.14 (2H), 2.87-2.92 (m, 1H), 2.96-3.01 (m, 1H). 3.11-3.15 (m, 1H), 7.22-7.35 (5H).

Provenance & Evidence