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

HRID 239763Notes

Reaction equation

HRID 239763 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 11908838(1S,2S)-trans-2-Benzyloxy-cyclohexylamine

Product 1

HCID 160359503-{[(1s,2s)-2-(Benzyloxy)cyclopentyl]amino}-1-propanesulfonic acidYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1S,2S)-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, washed with acetone (2×20 mL) and dried in the vacuum oven (50° C.), affording the title compound (1.15 g, 75%). 1H NMR (D2O, 500 MHz) δ ppm 7.34 (m, 5H), 4.62 (d, 1H, J=11.2 Hz), 4.42 (d, 1H, J=11.2 Hz), 3.40 (m, 1H), 2.97 (m, 2H), 2.90 (m, 1H), 2.76 (t, 2H, J=6.5 Hz), 2.26 (m, 1H), 1.92 (m, 3H), 1.66 (m, 2H), 1.18 (m, 4H). 13C NMR (D2O, 125 MHz) δ ppm 137.22, 129.34, 129.11, 128.84, 76.74, 70.26, 60.84, 48.02, 42.74, 29.49, 26.43, 23.57, 23.02, 21.53. [α]D=+74.8° (c=0.00207 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 (2×20 mL)
  4. customdried in the vacuum oven (50° C.)

Sources & evidence

ORD record
ord-73c6d687661f4fedbba3598b87985a9f
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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