Propane sultone → 1-Propanesulfonic acid, 3-[(2,2-dimethylpropyl)amino]-

HRID 239740Notes

Reaction equation

HRID 239740 reaction equation
[CH2:1]([NH2:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH2:7]1[CH2:13][S:10](=[O:12])(=[O:11])[O:9][CH2:8]1>O1CCCC1>[CH2:1]([NH:6][CH2:8][CH2:7][CH2:13][S:10]([OH:12])(=[O:11])=[O:9])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 79882Neopentylamine

Product 1

HCID 112527901-Propanesulfonic acid, 3-[(2,2-dimethylpropyl)amino]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of neopentylamine (8.5 g, 98 mmol) in tetrahydrofuran (75 mL) was slowly added a solution of 1,3-propane sultone (11.5 g, 93 mmol) in THF (20 mL). The solution was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×50 mL). The solid was suspended in EtOH (150 mL). The suspension was stirred at reflux for 15 minutes. The solid product was collected by filtration, washed with acetone (2×50 mL), and dried in vacuo, to afford compound DL (13.3 g, 69%). 1H NMR (D2O, 500 MHz) 8 ppm 3.09 (t, 2H, J=7.3 Hz), 2.89 (t, 2H, J=7.3 Hz), 2.78 (s, 2H), 2.04 (m, 2H), 0.901 (s, 9H). 13C NMR (D2O, 125 MHz) 8 ppm 59.44, 48.31, 47.83, 29.91, 26.42, 21.06. ES-MS 208 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetone (2×50 mL)
  4. stirringThe suspension was stirred
  5. temperatureat reflux for 15 minutes
  6. filtrationThe solid product was collected by filtration
  7. washwashed with acetone (2×50 mL)
  8. customdried in vacuo
  9. customto afford compound DL (13.3 g, 69%)

Sources & evidence

ORD record
ord-2e9050c1a87544138f36e2fe4d7fd3a0
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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