Carbon Dioxide → HCID 20714289, compound

HRID 2270092Notes

Reaction equation

HRID 2270092 reaction equation
[CH2:1]([C:3]1[C:12]([CH3:13])=[CH:11][C:10]2[C:5](=[C:6]([C@H:14](O)[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].[CH2:25]([N:27](CC)[CH2:28][CH3:29])[CH3:26].C(=O)=O.S(Cl)(C)(=O)=O.C(NCC)C>CC(C)=O.C(Cl)(Cl)Cl.C(OCC)C>[CH2:1]([C:3]1[C:12]([CH3:13])=[CH:11][C:10]2[C:5](=[C:6]([C@@H:14]([N:27]([CH2:28][CH3:29])[CH2:25][CH3:26])[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2]

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 8021DiethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20714291HCID 20714291, compound

Product 1

HCID 20714289HCID 20714289, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

1.85 g (5.35 mmol) of (+)-2-ethyl-3-methyl-8-(1(S)-hydroxy-2-[tert-butyldimethylsilyloxy]ethyl)-quinoline, 65 ml of ethyl ether and 1.33 ml (9.6 mmol) of triethylamine are introduced into a 250 ml round-bottomed flask. The mixture is cooled to −30° C. on a bath of cardice in acetone and 0.67 g (8.53 mmol) of mesyl chloride is added. The cooling bath is removed and the reaction mixture is allowed to warm to room temperature over 30 minutes. 100 ml of water are added and the resulting mixture is extracted with ethyl ether (3×50 ml). The organic phases are combined, dried over magnesium sulphate and concentrated. A portion of the residue (0.8 g of the 2.5 g obtained) is transferred, without further purification, into a 50 ml three-necked flask fitted with a condenser. 2.5 ml (34.6 mmol) of diethylamine and 3 ml of chloroform are added and this mixture is refluxed for 16 hours. The reaction mixture is cooled to room temperature and concentrated under vacuum, 50 ml of water are added and the resulting mixture is extracted with ethyl ether (3×30 ml). The organic phases are combined, dried over magnesium sulphate and concentrated under vacuum. The residue is purified by chromatography on a column of silica (elution solvent: 10% methanol in dichloromethane). 0.45 g (yield: 60%) of (+)-2-ethyl-3-methyl-8-(1(R)-diethylamino-2-[tert-butyldimethylsilyloxy]-ethyl)quinoline is obtained in the form of an oil.

Workup

  1. additionis added
  2. customThe cooling bath is removed
  3. addition100 ml of water are added
  4. extractionthe resulting mixture is extracted with ethyl ether (3×50 ml)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customA portion of the residue (0.8 g of the 2.5 g obtained)
  8. customis transferred, without further purification, into a 50 ml three-necked flask
  9. customfitted with a condenser
  10. temperaturethis mixture is refluxed for 16 hours
  11. temperatureThe reaction mixture is cooled to room temperature
  12. concentrationconcentrated under vacuum, 50 ml of water
  13. additionare added
  14. extractionthe resulting mixture is extracted with ethyl ether (3×30 ml)
  15. dry with materialdried over magnesium sulphate
  16. concentrationconcentrated under vacuum
  17. customThe residue is purified by chromatography on a column of silica (elution solvent: 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ba7cfeee236e4b16bed896a076956deb
Source dataset
uspto-grants-2001_12
Patent number
US06331549B1

Reaction notes

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