Potassium Carbonate → HCID 10203636, compound

HRID 966507Notes

Reaction equation

HRID 966507 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([O:13]S(C2C(C)=CC=CC=2)(=O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][C:25]1[NH:26][C:27]2[C:32]([C:33]=1[C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])=[CH:31][C:30](O)=[CH:29][CH:28]=2.C(=O)([O-])[O-].[K+].[K+].CCCCCC.C(OCC)(=O)C>C(#N)C.CN(C=O)C>[CH2:37]([O:36][C:34]([C:33]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:13][CH:10]3[CH2:11][CH2:12][N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:9]3)[CH:31]=2)[NH:26][C:25]=1[CH3:24])=[O:35])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 109239755-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl esterHCID 21226206Ethyl acetate hexaneHCID 862521471-Benzyl-3-toluenesulfonyloxypyrrolidine

Product 1

HCID 10203636HCID 10203636, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

1-benzyl-3-toluenesulfonyloxypyrrolidine (0.662 g, 2.00 mmol, 1.0 eq, see Bio. Org. & Med. Chem. Lett., 1999;9:1379) was dissolved in dry acetonitrile (20 mL) and DMF (1 mL), and treated with 2-methyl-3-benzyloxycarbonyl-5-hydroxyindole (0.562 g, 2.00 mmol, 1 cq) and potassium carbonate (0.276 g, 2.0 mmol, 1.0 eq.). The reaction was heated to reflux and followed by TLC (hexane/ethyl acetate 1/1). After 24 hours, the reaction was loaded directly on silica gel and chromatographed (hexane/ethyl acetate 1/1) to afford a yellow oil: 0.162 g (18% yield). This was converted to the corresponding hydrochloride salt: LC/MS (ESI+) 441 (M+1), Anal. (C28H28N2O3.HCl.1.6H2O) C, H, N.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customchromatographed (hexane/ethyl acetate 1/1)
  4. customto afford a yellow oil

Sources & evidence

ORD record
ord-5fb0ba0e14e54378b20f2d779a2a02fe
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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