Triethylamine → Methanesulfonic acid 2-(2-methoxy-phenyl)-cyclohexylmethyl ester

HRID 418908Notes

Reaction equation

HRID 418908 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH2:15][OH:16].[CH3:17][S:18](Cl)(=[O:20])=[O:19].CNC1C=CC=C(NC)N=1.CCN(CC)CC>[Cl-].[Na+].O.O.ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH2:15][O:16][S:18]([CH3:17])(=[O:20])=[O:19]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 111943672-N,6-N-dimethylpyridine-2,6-diamineHCID 66651820[2-(2-Methoxy-phenyl)-cyclohexyl]-methanol

Product 1

HCID 72309397Methanesulfonic acid 2-(2-methoxy-phenyl)-cyclohexylmethyl esterYield 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Combine [2-(2-methoxy-phenyl)-cyclohexyl]-methanol (0.725 g, 3.29 mmol), methanesulfonyl chloride (0.415 g, 3.62 mmol), 2,6-dimethylaminopyridine (80.0 mg, 0.66 mmol), Et3N (1.0 mL, 7.24 mmol), and dichloromethane (30.0 mL) at 0° C. After 20 min stir at room temperature under nitrogen. Reaction stirred for 18 hours then add water and brine. Separate layers and dry over anhydrous sodium sulfate. Concentrate and flash chromatography using 5 to 30% ethyl acetate/hexanes to yield the titled compound (0.810 g, 83%). TLC Rf=0.25 in 30% ethyl acetate/hexanes. 1H NMR (CDCl3): 7.2 (m, 1H), 7.1 (m, 1H), 6.9 (m, 2H), 4.3 (t, 1H, J=10.0 Hz), 3.9 (m, 4H), 3.3 (m, 1H), 2.8 (s, 3H), 2.6 (m, 1H), 1.8 (m, 6H), 1.5 (m, 2H).

Workup

  1. customat 0° C
  2. customReaction
  3. stirringstirred for 18 hours
  4. dry with materialSeparate layers and dry over anhydrous sodium sulfate
  5. concentrationConcentrate

Sources & evidence

ORD record
ord-169c08e88f7f494aa7eb9bc8a6b71c94
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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