Ethylene carbonate → HCID 22873792, compound

HRID 1683871Notes

Reaction equation

HRID 1683871 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:17][C@H:18]1[CH2:22][CH2:21][CH2:20][NH:19]1)(=[O:5])=[O:4])[CH3:2].C1(=O)O[CH2:26][CH2:25][O:24]1>CN(C)C=O>[CH2:1]([S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:17][C@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[CH2:26][CH2:25][OH:24])(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 7303Ethylene carbonateHCID 22873790HCID 22873790, compound

Product 1

HCID 22873792HCID 22873792, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 5-(2-ethylsulphonylethyl)-3-(2(R)-pyrrolidinylmethyl)-1H-indole (Preparation 5; 350 mg, 1.1 mmol) in dry dimethylformamide (10 ml) at room temperature under nitrogen was added ethylene carbonate (160 mg, 1.8 mmol). The mixture was heated at 120° C. for 18 hours, allowed to cool, then partitioned between ethyl acetate and water. The organic phase was separated, washed with water (3×), dried (Na2SO4) and evaporated under reduced pressure to give a foam. Purification by column chromatography on silica gel, eluting initially with dichloromethane followed by a gradient of 0.880 aqueous ammonia:ethanol: dichloromethane (0:10:90 to 0.5:10:90), afforded the title compound as gum. Rf 0.35 (SS 4). Found: C,62.29; H,7.73; N,7.23. C19H28N2O3S; 0.05 CH2Cl2 requires C,62.04; H,7.68; N,7.60%. δ(CDCl3): 1.35(3H,t), 1.50-1.90(5H,m), 2.30(1H,m), 2.50(1H,m), 2.70(1H,m), 2.80-3.35(10H,m), 3.60-3.75(2H,m), 5.30(0.10H,s,CH2Cl2), 7.00(1H,d), 7.05(1H,s), 7.25(1H,d), 7.40(1H,s), 8.25(1H,br s).

Workup

  1. temperatureto cool
  2. custompartitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. washwashed with water (3×)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customto give a foam
  8. customPurification by column chromatography on silica gel
  9. washeluting initially with dichloromethane

Sources & evidence

ORD record
ord-e0b7ee6589a54bef9c8cdfd63a44dccd
Source dataset
uspto-grants-1997_06
Patent number
US05639779

Reaction notes

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