Triethylamine → Methanesulfonic acid 2-(2,5-dimethoxy-phenyl)-cyclopentylmethyl ester

HRID 418923Notes

Reaction equation

HRID 418923 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][OH:17].CNC1C=CC=C(NC)N=1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][O:17][S:36]([CH3:35])(=[O:38])=[O:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 111943672-N,6-N-dimethylpyridine-2,6-diamineHCID 66652073[2-(2,5-Dimethoxy-phenyl)-cyclopentyl]-methanol

Product 1

HCID 72309417Methanesulfonic acid 2-(2,5-dimethoxy-phenyl)-cyclopentylmethyl esterYield 101.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve [2-(2,5-dimethoxy-phenyl)-cyclopentyl]-methanol (3.6 g, 15 mmol) in dichloromethane (94 ml), add 2,6-dimethylaminopyridine (0.4 g, 0.31 mmol), add triethylamine (4.7 ml, 33.5 mmol), cool to 0° C., add methanesulfonyl chloride (1.9 g, 17 mmol), remove ice bath and stir 2 hours at room temperature. Quench with water and ethyl acetate, separate layers, wash with brine, dry and concentrate to give the title compound (4.8 g, 100%): 1H NMR (CDCl3) δ 6.78-6.69 (m, 3H), 3.86-3.82 (m, 1H), 3.79 (s, 3H), 3.76 (s, 3H), 3.68-3.64 (m,1H), 3.53-3.47 (m, 1H), 2.83-2.76 (m, 1H), 2.69 (s,3H), 1.97-1.88 (m, 3H), 1.67-1.60 (m,3H).

Workup

  1. customremove ice bath
  2. customQuench with water and ethyl acetate
  3. customseparate layers
  4. washwash with brine
  5. customdry
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-04c0f51a610342d6b2519fe0387655d7
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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