Dimethylformamide → Pentyl methanesulfonate

To a stirred solution of 231 mg (5.79 mmol, 60% disp.) of NaH in 22 mL of DMF was added 2.05 g (4.45 mmol) of 5-(4'-hydroxyphenyl)-7-(dimethylamino)tetrahydrobenzothiepine-1,1-dioxide (obtained from Example 1402, Step 10), and the resulting solution was stirred at ambient temperature for 1 hour. To the mixture was added 18.02 g (55.63 mmol) of 1,5-diiodopentane and the solution was stirred overnight at ambient temperature. DMF was removed by high vacuum and the residue was extracted with ethyl acetate and washed with brine. The extract was dried over MgSO4, and the concentrated residue was purified by column chromatography to give the pentyl mesylate intermediate: 1H NMR (CDCl3) δ 0.90(q, 6H), 1.05-2.0 (m, 17H), 2.2 (t, 1H), 2.8 (s, 6h), 3.0 (q, 2H), 3.22 (t, 2H), 3.95 (t, 2H), 4.1 (s, 1H), 5.42 (s, 1H), 6.1 (d, 1H), 6.6 (d, 1H), 6.9 (d, 2H), 7.4 (d, 2H), 7.9 (d, 1H).

1. stirringthe solution was stirred overnight at ambient temperature
2. customDMF was removed by high vacuum
3. extractionthe residue was extracted with ethyl acetate
4. washwashed with brine
5. dry with materialThe extract was dried over MgSO4
6. customthe concentrated residue was purified by column chromatography

ORD record

ord-312dd2c2dcdf40de866fb7c444eb56c3

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05994391