2-Amino-2-methyl-1-propanol → 1-Propanesulfonic acid, 3-[(2-hydroxy-1,1-dimethylethyl)amino]-

HRID 239736Notes

Reaction equation

HRID 239736 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[CH2:7]1[CH2:13][S:10](=[O:12])(=[O:11])[O:9][CH2:8]1>O1CCCC1>[CH3:5][C:2]([NH:1][CH2:8][CH2:7][CH2:13][S:10]([OH:12])(=[O:11])=[O:9])([CH3:6])[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 14264Propane sultone

Product 1

HCID 112066121-Propanesulfonic acid, 3-[(2-hydroxy-1,1-dimethylethyl)amino]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-2-methyl-1-propanol (2.0 g, 21.4 mmol) in tetrahydrofuran (15 mL) was added 1,3-propane sultone (2.66 g, 21.4 mmol). The mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The crude product was collected by filtration, washed with acetone (2×25 mL). The solid was suspended in EtOH (50 mL). The suspension was stirred at reflux for 5 minutes. The solid was collected by filtration and dried in a vacuum oven (50° C.), affording compound DH (2.5 g, 58%): 1H NMR (D2O, 500 MHz) 8 ppm 3.48 (s, 2H), 3.04 (t, 2H, J=7.8 Hz), 2.90 (t, 2H, J=7.3 Hz), 2.00 (m, 2H), 1.18 (s, 6H). 13C NMR (D2O, 125 MHz) 8 ppm 64.88, 60.27, 48.19, 40.10, 21.92, 20.02. ES-MS 210 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe crude product was collected by filtration
  3. washwashed with acetone (2×25 mL)
  4. stirringThe suspension was stirred
  5. temperatureat reflux for 5 minutes
  6. filtrationThe solid was collected by filtration
  7. customdried in a vacuum oven (50° C.)
  8. customaffording compound DH (2.5 g, 58%)

Sources & evidence

ORD record
ord-34e4ed37001f4add81f630627a4a1cd1
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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