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

HRID 239764Notes

Reaction equation

HRID 239764 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:14][CH2:13][CH2:12]C[C@H:10]1[NH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]1[CH2:22][S:19](=[O:21])(=[O:20])[O:18][CH2:17]1>O1CCCC1>[CH2:1]([O:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][C@H:10]1[NH:15][CH2:17][CH2:16][CH2:22][S:19]([OH:21])(=[O:20])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 11863651(1R,2R)-trans-2-Benzyloxy-cyclohexylamine

Product 1

HCID 160359513-{[(1r,2r)-2-(Benzyloxy)cyclopentyl]amino}-1-propanesulfonic acidYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,2R)-2-benzyloxycyclohexylamine (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 (2×35 mL). The solid was suspended in 80% acetone/EtOH (200 mL). The suspension was stirred at reflux for 30 seconds before the solid was filtered and dried in the vacuum oven (50° C.), affording the title compound (844 mg. 55%). 1H NMR (D2O, 500 MHz) δ ppm 7.32 (m, 5H), 4.60 (d, 1H, J=11.2 Hz), 4.40 (d, 1H, J=11.2 Hz), 3.39 (m, 1H), 2.94 (m, 2H), 2.85 (m, 1H), 2.74 (t, 2H, J=6.5 Hz), 2.24 (m, 1H), 1.90 (m, 3H), 1.64 (m, 2H), 1.14 (m, 4H). 13C NMR (D2O, 125 MHz) δ ppm 137.35, 129.28, 129.19, 128.90, 76.90, 70.35, 60.97, 48.12, 42.90, 29.59, 26.53, 23.64, 23.09, 21.63. [α]D=−68.9° (c=0.0026 in water). ES-MS 326 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetone (2×35 mL)
  4. stirringThe suspension was stirred
  5. temperatureat reflux for 30 seconds before the solid
  6. filtrationwas filtered
  7. customdried in the vacuum oven (50° C.)

Sources & evidence

ORD record
ord-eafe413c4fac4a54a8f83b724032a304
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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