Methyl iodide → HCID 178497883, compound

HRID 1255186Notes

Reaction equation

HRID 1255186 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([CH3:18])[CH:9]=2)[CH2:4][CH2:3]1.[C:19](C1C=CC=C(C(C)(C)C)N=1)(C)(C)C.IC>C(Cl)Cl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:19][O:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([CH3:18])[CH:9]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 685102,6-Di-tert-butylpyridineHCID 178497881HCID 178497881, compound

Product 1

HCID 178497883HCID 178497883, compound

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the title compound from Example 13 Step E (234 mg, 0.942 mmol) in DCM (4.7 mL) were added 2,6-di-tert-butylpyridine (0.318 mL, 1.41 mmol) and silver trifluoromethanesulfonate (266 mg, 1.04 mmol). The resulting solution was cooled to 0° C., and iodomethane (0.071 mL, 1.13 mmol) was added. After 30 min, the reaction mixture was allowed to warm to ambient temperature and was held at this temperature for 3 h, whereupon it was filtered through Celite, rinsing with DCM. The reaction mixture was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30% EtOAc in hexanes, then 30 to 100% EtOAc in hexanes) provided the title compound. Analytical data for the major isomer (trans cyclohexyl): LCMS m/z 263.17 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.85 (d, J=8.5 Hz, 1H), 7.08-7.06 (m, 2H), 3.86 (s, 3H), 3.38 (s, 3H), 3.24-3.17 (m, 1H), 2.58 (s, 3H), 2.49 (dt, J=12.0, 3.5 Hz, 1H), 2.21-2.18 (m, 2H), 1.94-1.92 (m, 2H), 1.54-1.46 (m, 2H), 1.39-1.30 (m, 2H).

Workup

  1. temperatureto warm to ambient temperature
  2. waitwas held at this temperature for 3 h, whereupon it
  3. filtrationwas filtered through Celite
  4. washrinsing with DCM
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. customPurification by flash chromatography on silica gel (0 to 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-0fa9133987f6400285d5cfd80d94ccff
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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