1,2-Ethanediol, 1-phenyl-, 2-(4-methylbenzenesulfonate), (1R)-

White to off-white powder

General procedure: A mixture of (-)-cis-N-normetazocine (1equiv), the appropriate tosylate intermediates (1-5, 1.5equiv), NaHCO3 (1.5equiv) and a catalytic amount of KI was stirred in DMF at 65C for 24h. After cooling, the reaction mixture was filtered and concentrated under vacuum to remove DMF. The resulting residue was purified by flash chromatography on silica gel column using as eluent CH2Cl2/CH3OH (97:3, v/v). The free bases were converted to the hydrochloride salts by dissolving the free bases in minimum amount of methanol and adding 1N HCl in Et2O to the solution. 4.3.1 (2R, 6R, 11R)-3-((R)-2-Hydroxy-2-phenylethyl)-6, 11-dimethyl-1, 2, 3, 4, 5, 6-hexahydro-2, 6-methanobenzo[d]azocin-8-ol (6) White solid (65%); mp: 167-169 C; - 54.8 (c 1.0, MeOH). 1H NMR (CDCl3, free base) delta 7.42-7.40 (m, 2H), 7.32-7.29 (m, 2H), 7.25-7.22 (m, 1H), 6.96 (m, 1H, J = 8.2 Hz), 6.68 (m, 1H, J = 2.0 Hz), 6.58 (dd, 1H, J = 8.0, 2.0 Hz), 5.09 (d, 1H), 3.41-3.32 (m, 2H), 3.21-3.05 (m, 4H), 2.72-2.67 (m, 1H), 2.13-2.12 (m, 1H), 2.06-2.00 (m, 1H), 1.50-1.48 (m, 1H), 1.34 (s, 3H), 0.90 (d, 3H). 13C NMR (CHCl3, free base) delta 154.09, 143.06, 142.34, 128.65, 128.44, 127.98, 127.4, 126.01, 112.96, 112.18, 68.69, 61.68, 55.57, 46.95, 41.62, 41.24, 36.31, 25.42, 25.18, 14.07. MS m/z [M]+ 337, 5. Anal. Calcd for C22H27NO2·HCl: C, 70, 7%; H, 7, 5%; N, 3, 7%. Found: C, 70, 4%; H, 7, 7%; N, 3, 6%.General procedure: A solution of monotosylate (1.0 eq), tetrabutylammonium iodide (0.05 eq) and sodium azide (3.0 eq) in DMF was heatedat 80-90 C for 3-4 h. After completion of the reaction (TLC), reaction mixturewas cooled to 0 C and water (5 mL) was added. The aqueous layer was extractedwith ethyl acetate (3x35 mL). The combined organic layers were washed withbrine (2x20 mL), dried over anhydrous Na2SO4, filtered, and concentrated. The concentrate was purified by silica gel columnchromatography (100-200 mesh) using EtOAc/petroleum ether (3:7) to afford thedesired product in 80-95% yield.

Molecular Weight:292.4
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:292.07693016
Monoisotopic Mass:292.07693016
Topological Polar Surface Area:72
Heavy Atom Count:20
Complexity:373
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes