1,4-Butane sultone → HCID 58794628, compound

HRID 239802Notes

Reaction equation

HRID 239802 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH2:11])[CH2:8]2.[CH2:12]1[CH2:19][O:18][S:15](=[O:17])(=[O:16])[CH2:14][CH2:13]1>O1CCOCC1>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][CH2:19][CH2:12][CH2:13][CH2:14][S:15]([OH:18])(=[O:17])=[O:16])[CH2:8]2

Participants

4

Reactant 2

HCID 154111,4-Butane sultoneHCID 253322-Aminoadamantane

Product 1

HCID 58794628HCID 58794628, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-adamantanamine (1.06 g, 7.0 mmol) in 1,4-dioxane (6 mL) was added 1,4-butane sultone (955 mg, 6.7 mmol). The solution was stirred at reflux for 5 hours. The reaction was cooled to room temperature. The solid was collected by filtration. It was suspended in EtOH (25 mL) and the mixture was heated to reflux for 1 minute before the solid was filtered. It was washed with EtOH (1×15 mL) and dried in vacuo. Yield: 55%. 1H NMR (D2O, 500 MHz) δ ppm 3.29 (m, 1H), 2.97 (m, 2H), 2.83 (m, 2H), 2.02 (m, 2H), 1.83 (m, 2H), 1.68 (m, 14H). 13C NMR (D2O, 125 MHz) δ ppm 63.07, 50.25, 45.03, 36.55, 36.31, 29.85, 29.05, 26.68, 26.41, 24.47, 21.61. ES-MS 286 (M−1).

Workup

  1. temperatureat reflux for 5 hours
  2. filtrationThe solid was collected by filtration
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 1 minute before the solid
  5. filtrationwas filtered
  6. washIt was washed with EtOH (1×15 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-23d4b2eb0d04413cb1aecac04d636d0b
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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