Sodium Hydroxide → HCID 58931828, compound

HRID 239804Notes

Reaction equation

HRID 239804 reaction equation
[CH2:1]1[CH:5]2[CH2:6][CH:7]([NH2:8])[CH:3]([CH2:4]2)[CH2:2]1.[OH-].[Na+].Cl[CH2:12][CH:13]([OH:19])[CH2:14][S:15]([OH:18])(=[O:17])=[O:16].[Na]>O1CCOCC1.O>[CH:3]12[CH2:4][CH:5]([CH2:1][CH2:2]1)[CH2:6][CH:7]2[NH:8][CH2:12][CH:13]([OH:19])[CH2:14][S:15]([OH:18])(=[O:17])=[O:16]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 313603-Chloro-2-hydroxypropane-1-sulfonic acidHCID 98480Exo-2-bornanamineHCID 5360545Sodium

Product 1

HCID 58931828HCID 58931828, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To an 80° C. solution of exo-2-aminonorbornane (910 mg, 8.2 mmol) and sodium hydroxide (242 mg, 6.1 mmol) in 1,4-dioxane (4 mL) and water (4 mL) was added via syringe pump (1 hour addition) a solution of 3-chloro-2-hydroxy-propane sulfonic acid, sodium salt (1.09 g, 5.5 mmol) in 1,4-dioxane (0.5 mL) and water (5.5 mL). The solution was stirred at 80° C. for an additional 5 hours. The reaction was cooled to room temperature. The solvent was evaporated under reduced pressure. The solid was suspended in EtOH (25 mL). The mixture was heated to reflux for 1 minute. The solid was recovered by filtration and it was passed through an ion exchange column (Dowex 50×8, 100 g, solvent: water). The product was recrystallized in EtOH/water (99/1). Yield: 17%. 1H NMR (D2O, 500 MHz) δ ppm 4.25 (m, 1H), 3.25 (m, 2H), 3.01 (m, 4H), 2.39 (m, 1H), 2.27 (m, 1H), 1.69 (m, 1H), 1.51 (m, 1H), 1.38 (m, 3H), 1.19 (m, 1H), 1.07 (m, 2H). 13C (D2O, 125 MHz) δ ppm 63.66, 63.50, 62.21, 61.98, 54.94, 50.11, 50.04, 39.26, 39.21, 36.02, 35.97, 35.91, 35.80, 34.70, 34.61, 27.11, 27.08, 26.50, 26.45. ES-MS 250 (M−1).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customThe solvent was evaporated under reduced pressure
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 1 minute
  5. filtrationThe solid was recovered by filtration and it
  6. customThe product was recrystallized in EtOH/water (99/1)

Sources & evidence

ORD record
ord-1cfc1a7540ee4cf88ccf845ea19da9c4
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

Loading…