Potassium Iodide → HCID 59526803, compound

HRID 1920699Notes

Reaction equation

HRID 1920699 reaction equation
[I-].[K+].CC1C=CC(S(O[CH2:14][CH2:15][F:16])(=O)=O)=CC=1.[CH2:17]([N:24]1[CH2:28][CH2:27][C@@H:26]([C@@H:29]([NH2:31])[CH3:30])[CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:17]([N:24]1[CH2:28][CH2:27][C@@H:26]([C@@H:29]([NH:31][CH2:14][CH2:15][F:16])[CH3:30])[CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 10081651HCID 10081651, compound

Product 1

HCID 59526803HCID 59526803, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Potassium iodide (0.71 g, 4.27 mmol) and 2-fluoroethyl 4-methylbenzenesulfonate (0.93 g, 4.27 mmol) (Kopka, et al., 2006) are added to a solution of (S)-1-((R)-1-benzylpyrrolidin-3-yl)ethanamine (0.83 g, 4.06 mmol) (Shroeder, et al., 1992) in DMF (10 mL). The reaction mixture is heated for 2 h at 100° C. and evaporated under reduced pressure. The residue is purified by column chromatography (chloroform-ethanol-triethylamine=30:1:1) to afford the desired product (0.51 g, 50%) as a brown oil. 1H NMR (CDCl3): δ 1.09 (d, J=6.3 Hz, 3H, methyl), 1.55 (m, 1H), 1.96 (m, 1H), 3.15-2.15 (m, 9H), 3.65 (s, 2H, —CH2Ph), 4.46 (m, 1H, —CHF), 4.61 (m, 1H, —CHF), 7.31 (m, 5H, ArH). 13C NMR (CDCl3): δ 18.1, 27.5, 43.8, 53.9, 56.7, 57.5, 60.4, 82.4, 84.6, 126.6, 128.1, 128.5, 139.0. LCMS: m/z calcd for C15H23FN2 ([M]+) 250. found 251 ([M+H]+).

Workup

  1. customevaporated under reduced pressure
  2. customThe residue is purified by column chromatography (chloroform-ethanol-triethylamine=30:1:1)

Sources & evidence

ORD record
ord-8cf8c99137334fc1a7825534423a4666
Source dataset
uspto-grants-2012_05
Patent number
US08173636B2

Reaction notes

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