Sodium Iodide → HCID 54314874, compound

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).

1. customThe reaction was quenched with H2O and 50 mL of 1.0 N HCl
2. extractionThe quenched mixture was extracted 3× with CH2Cl2
3. washThe organic extracts were washed with sat'd NaCl
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationthe filtrate concentrated
7. temperaturewas heated
8. temperatureat reflux for 2 h
9. temperatureThe reaction mixture cooled
10. concentrationconcentrated
11. additionThe residue was diluted with H2O
12. extractionextracted 3× with CH2Cl2
13. washThe extracts were washed with sat'd NaCl
14. dry with materialdried over Na2SO4
15. filtrationfiltered
16. concentrationthe filtrate concentrated
17. customThe residue was purified by flash chomatography on 50 g of silica eluting with 0-20% EtOAc/hexanes (v/v)

ORD record

ord-0f83a73340014b3a9cd663aefd052e43

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265434B1