Heptaminol → 3-[(6-Hydroxy-6-methylheptan-2-yl)amino]propane-1-sulfonic acid

HRID 239787

Reaction equation

HRID 239787 reaction equation
[NH2:1][CH:2]([CH3:10])[CH2:3][CH2:4][CH2:5][C:6]([CH3:9])([OH:8])[CH3:7].[CH2:11]1[CH2:17][S:14](=[O:16])(=[O:15])[O:13][CH2:12]1>C(#N)C>[OH:8][C:6]([CH3:9])([CH3:7])[CH2:5][CH2:4][CH2:3][CH:2]([NH:1][CH2:12][CH2:11][CH2:17][S:14]([OH:16])(=[O:15])=[O:13])[CH3:10]

Participants

4

Reactant 2

HCID 3590HeptaminolHCID 14264Propane sultone

Product 1

HCID 160361833-[(6-Hydroxy-6-methylheptan-2-yl)amino]propane-1-sulfonic acidYield 70.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-amino-2-methyl-2-heptanol (2.5 g, 17.2 mmol) in acetonitrile (22 mL) was added 1,3-propane sultone (2.0 g, 16.4 mmol). The solution was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid material was filtered and washed with acetonitrile (2×20 mL). The solid was dissolved in 20% MeOH (75 mL). Dowex Marathon C ion exchange resin (strongly acidic) was added to the solution. The suspension was stirred for 15 minutes before the resin was removed by filtration. The filtrate was evaporated under reduced pressure. The solid was suspended in acetone (150 mL), and then the solid material was filtered and dried in vacuo, affording the title compound (3.08 g, 70%). 1H NMR (D2O, 500 MHz) δ ppm 3.19 (m, 1H), 3.08 (m, 2H), 2.88 (t, 2H, J=7.3 Hz), 1.99 (m, 2H), 1.60 (m, 2H), 1.36 (m, 4H), 1.18 (d, 3H, J=6.8 Hz), 1.07 (s, 6H). 13C (D2O, 125 MHz) δ ppm 71.63, 54.73, 48.08, 43.46, 42.27, 32.97, 27.78, 27.73, 21.64, 19.67, 15.43. ES-MS 268 (M+1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid material was filtered
  3. washwashed with acetonitrile (2×20 mL)
  4. dissolutionThe solid was dissolved in 20% MeOH (75 mL)
  5. additionDowex Marathon C ion exchange resin (strongly acidic) was added to the solution
  6. stirringThe suspension was stirred for 15 minutes before the resin
  7. customwas removed by filtration
  8. customThe filtrate was evaporated under reduced pressure
  9. filtrationthe solid material was filtered
  10. customdried in vacuo

Sources & evidence

ORD record
ord-d64b1f084f644a3f8a13bf7c801f6912
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

Loading…