Triethylamine → HCID 87318941, compound

HRID 909371Notes

Reaction equation

HRID 909371 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 bottom 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 a complete conversion. The reaction mixture was concentrated in vacuo then partitioned between EtOAc and 1 N HCl, the layers separated, the organics 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. customthen partitioned between EtOAc and 1 N HCl
  4. customthe layers separated
  5. dry with materialthe organics dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2ebb9ee62a7741ecbdf8339e7c49ce0b
Source dataset
uspto-grants-2011_09
Patent number
US08017788B2

Reaction notes

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