Triethylamine → HCID 87318941, compound

HRID 2355773Notes

Reaction equation

HRID 2355773 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[OH:13])=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:21][S:22](Cl)(=[O:24])=[O:23].CCOC(C)=O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[O:13][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 87316410HCID 87316410, compound

Product 1

HCID 87318941HCID 87318941, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

trans-2-(6-Chloropyridin-3-yl)cyclopentanol (0.225 g, 1.14 mmol) was dissolved in CH2Cl2 (10 mL) in a 50 mL round bottomed flask, the solution cooled in an ice bath under nitrogen and treated with Et3N (0.172 g, 1.71 mmol, 0.24 mL) and methanesulfonyl chloride (0.163 g, 1.42 mmol, 0.11 ml) via syringe with stirring. After 1 h, TLC (hexanes:EtOAc/2:1) indicated complete conversion. The reaction mixture was concentrated in vacuo and then partitioned between EtOAc and 1 N HCl. The layers were separated and the organics was dried (Na2SO4), filtered and concentrated to give trans-methanesulfonic acid 2-(6-chloropyridin-3-yl)cyclopentyl ester (0.303 g, 97%) as an oil: LC/MS (ESI) m/z 275, 1H NMR (300 MHz, CDCl3) δ 8.28 (d, 1H, J=2.7 Hz), 7.56 (dd, 1H, J=8.1, 2.7 Hz), 7.3 (d, 1H, J=8.1 Hz), 4.93 (apparent q, 1H, J=5.7 Hz), 3.28 (apparent q, 1H, J=8.7 Hz), 2.86 (s, 3H), 2.26 (m, 2H), 2.10-1.80 (m, 3H), 1.73 (m, 1H).

Workup

  1. temperaturethe solution cooled in an ice bath under nitrogen
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between EtOAc and 1 N HCl
  4. customThe layers were separated
  5. dry with materialthe organics was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-82b2dbb4c9934c5cba2be76d2cba6932
Source dataset
uspto-grants-2010_07
Patent number
US07754888B2

Reaction notes

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