Propane sultone → 3-{[(1r,2r)-2-(Benzyloxy)cyclopentyl]amino}-1-propanesulfonic acid

HRID 239761Notes

Reaction equation

HRID 239761 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[NH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]1[CH2:21][S:18](=[O:20])(=[O:19])[O:17][CH2:16]1>O1CCCC1>[CH2:1]([O:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[NH:14][CH2:16][CH2:15][CH2:21][S:18]([OH:20])(=[O:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 11863649(1R,2R)-trans-2-Benzyloxy-cyclopentylamine

Product 1

HCID 160359513-{[(1r,2r)-2-(Benzyloxy)cyclopentyl]amino}-1-propanesulfonic acidYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,2R)-2-benzyloxycyclopentylamine (1.0 g, 5.2 mmol) in tetrahydrofuran (12 mL) was slowly added 1,3-propanesultone (601 mg, 5.0 mmol). The solution was stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration and washed with acetone (2×15 mL). The product was suspended in EtOH and the solvent was evaporated (to remove THF residue). The solid was dried in vacuo, affording the title compound (717 mg, 46%). 1H NMR (D2O, 500 MHz) δ ppm 7.32 (m, 5H), 4.53 (d, 1H, J=11.2 Hz), 4.42 (d, 1H, J=11.2 Hz), 4.02 (m, 1H), 3.36 (m, 1H), 3.01 (t, 2H, J=7.8 Hz), 2.81 (t, 2H, J=7.8 Hz), 2.01 (m, 4H), 1.65 (m, 3H), 1.49 (m, 1H). 13C NMR (D2O, 125 MHz) δ ppm 137.00, 129.07, 129.01, 128.77, 81.78, 71.81, 63.89, 48.02, 45.34, 29.93, 27.43, 21.61, 20.94. [α]D=−38.8° (c=0.00122 in water). ES-MS 314 (M+1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetone (2×15 mL)
  4. customthe solvent was evaporated
  5. custom(to remove THF residue)
  6. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-3357a593bd4f4485a3ed31b8ed37e6b6
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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