Triethylamine → HCID 87318941, compound

HRID 1931376Notes

Reaction equation

HRID 1931376 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-83f9f2b2089a4b7e93e7cb0eb2fc15a4
Source dataset
uspto-grants-2012_05
Patent number
US08188292B2

Reaction notes

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