Hydrochloric Acid → HCID 69422275, compound

HRID 1178875Notes

Reaction equation

HRID 1178875 reaction equation
CN.[C:3]1(=[O:8])[CH2:7][CH2:6][CH:5]=[CH:4]1.[C:9]1([CH3:19])[CH:14]=[CH:13][CH:12]=[C:11]([S:15](Cl)(=[O:17])=[O:16])[CH:10]=1.[CH2:20]([N:22]([CH2:25][CH3:26])CC)C.Cl>ClCCl.CN(C)C1C=CN=CC=1>[C:25]([O:8][CH2:3][CH3:7])(=[O:16])[CH3:26].[CH3:12][CH2:11][CH2:10][CH:9]([CH3:19])[CH3:14].[CH3:19][C:9]1[CH:10]=[C:11]([S:15]([N:22]([CH:5]2[CH2:6][CH2:7][C:3](=[O:8])[CH2:4]2)[CH3:20])(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 8471TriethylamineHCID 135882-Cyclopenten-1-oneHCID 27345953-Methylbenzenesulphonyl chloride

Product 2

HCID 21882781Isohexane ethyl acetateHCID 69422275HCID 69422275, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-4 °C

Procedure

Methylamine (2.0M in THF; 10 ml, 20 mmol) was added dropwise over 5 minutes to a solution of 2-cyclopenten-1-one (1.68 ml, 20 mmol) in dichloromethane (16 ml) cooled to −4° C. The resulting mixture was stirred at −4° C. to +1° C. for 1 hour 30 minutes then added to a solution of 3-toluenesulfonyl chloride (3.83 g, 20.1 mmol), triethylamine (2.8 ml, 20 mmol) and 4-dimethylaminopyridine (128.4 mg, 1.05 mmol) in dichloromethane (50 ml). The reaction mixture was stirred at 0° C. for 30 minutes, allowed to warm to room temperature over 30 minutes then stirred for a further 2 hours. The mixture was poured into 1M hydrochloric acid (100 ml), separated and the organic phase washed with saturated aqueous sodium hydrogen carbonate (100 ml). The organic phase was dried (MgSO4), concentrated in vacuo and the residue purified by flash chromatography, eluting with 1:3, 1:2 then 1:1 ethyl acetate-isohexane, to give the title compound (2.48 g, 46%) as an pale amber oil; δH (400 MHz, CDCl3) 1.89 (1H, m), 2.05 (1H, m), 2.10-2.22 (3H, m), 2.34 (1H, m), 2.44 (3H, s), 2.78 (3H, s), 4.60 (1H, m), 7.40 (2H, m), 7.60 (2H, m).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 30 minutes
  2. temperatureto warm to room temperature over 30 minutes
  3. stirringthen stirred for a further 2 hours
  4. customseparated
  5. washthe organic phase washed with saturated aqueous sodium hydrogen carbonate (100 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customthe residue purified by flash chromatography
  9. washeluting with 1:3, 1:2

Sources & evidence

ORD record
ord-cf6cf60ef673421b9e9933c16c9fa1c0
Source dataset
uspto-grants-2007_10
Patent number
US07276607B2

Reaction notes

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