Isoamylamine → 4-[(3-Methylbutyl)amino]butane-2-sulfonic acid

HRID 239805Notes

Reaction equation

HRID 239805 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[CH3:7][CH:8]1[S:12](=[O:14])(=[O:13])[O:11][CH2:10][CH2:9]1>O1CCCC1>[CH3:4][CH:3]([CH3:5])[CH2:2][CH2:1][NH:6][CH2:10][CH2:9][CH:8]([S:12]([OH:14])(=[O:13])=[O:11])[CH3:7]

Participants

4

Reactant 2

HCID 7894IsoamylamineHCID 707161,2-Oxathiolane, 3-methyl-, 2,2-dioxide

Product 1

HCID 589318554-[(3-Methylbutyl)amino]butane-2-sulfonic acidYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a hot solution of isoamylamine (2.0 g, 22.9 mmol) in tetrahydrofuran (THF, 11 mL) was added via syringe pump (2 hour addition) a solution of 2,4-butane sultone (3.1 g, 21.8 mmol in THF (total of 5 mL)). The solution was stirred at reflux for an additional 2 hours. The reaction was cooled to room temperature. The solid was recovered by filtration and it was washed with THF (25 mL) and acetone (25 mL). The solid was dissolved in water (20 mL) and Dowex 50×8 (10 g) was suspended in the solution. The mixture was stirred for 15 minutes and the resin was filtered. The solvent was evaporated under reduced pressure. Yield: 28%. 1H NMR (H2O, 500 MHz) δ ppm 3.07 (t, 2H, J=7.8 Hz), 2.92 (t, 2H, J=7.8 Hz), 2.87 (m, 1H), 2.06 (m, 1H), 1.77 (m, 1H), 1.51 (m, 1H), 1.42 (m, 2H), 1.18 (d, 3H, J=6.8 Hz), 0.78 (d, 3H, J=6.3 Hz). 13C(H2O, 125 MHz) δ ppm 53.21, 46.32, 45.37, 34.36, 28.16, 25.35, 21.51, 14.79. ES-MS 224 (M+1).

Workup

  1. temperatureat reflux for an additional 2 hours
  2. filtrationThe solid was recovered by filtration and it
  3. washwas washed with THF (25 mL) and acetone (25 mL)
  4. dissolutionThe solid was dissolved in water (20 mL)
  5. stirringThe mixture was stirred for 15 minutes
  6. filtrationthe resin was filtered
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2274e7ab564d47548c87835c81e53e32
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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