1,2-Oxathiolane, 3-methyl-, 2,2-dioxide → HCID 59771573, compound

HRID 239793

Reaction equation

HRID 239793 reaction equation
[CH2:1]1[CH:5]2[CH2:6][CH:7]([NH2:8])[CH:3]([CH2:4]2)[CH2:2]1.[CH3:9][CH:10]1[S:14](=[O:16])(=[O:15])[O:13][CH2:12][CH2:11]1>O1CCCC1>[CH:3]12[CH2:4][CH:5]([CH2:1][CH2:2]1)[CH2:6][CH:7]2[NH:8][CH2:12][CH2:11][CH:10]([S:14]([OH:16])(=[O:15])=[O:13])[CH3:9]

Participants

4

Reactant 2

HCID 707161,2-Oxathiolane, 3-methyl-, 2,2-dioxideHCID 98480Exo-2-bornanamine

Product 1

HCID 59771573HCID 59771573, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of exo-2-aminonorbornane (1.0 g, 9.0 mmol) in tetrahydrofuran (THF, 10 mL) was added 2,4-butane sultone (1.28 g, 9.3 mmol). The solution was stirred at reflux for 3 hours. The reaction was cooled to room temperature. The solid was collected by filtration, washed with THF (2×20 mL) and dried in vacuo. 1H NMR (DMSO, 500 MHz) δ ppm 8.43 (s (broad), 1H), 2.96 (m, 3H), 2.62 (m, 1H), 2.38 (m, 1H), 2.28, (m, 1H), 1.91 (m, 1H), 1.82 (m, 1H), 1.61 (m, 1H), 1.54 (m, 2H), 1.42 (m, 2H), 1.12 (m, 6H). 13C (DMSO, 125 MHz) δ ppm 60.92, 60.79, 53.61, 53.21, 44.55, 44.36, 39.80, 39.55, 36.27, 36.15, 36.11, 35.98, 35.19, 35.13, 29.62, 29.43, 28.07, 26.88, 17.56, 14.11. ES-MS 248 (M+1).

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with THF (2×20 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-45b730f9ad5b4cf39f54939210a94f65
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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