4-Chlorobenzenesulfonyl chloride → 4-chloro-N-(trans-2-hydroxymethylcyclopentyl)benzenesulfonamide

HRID 1011505Notes

Reaction equation

HRID 1011505 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][OH:8].C(N(CC)CC)C.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(OCC)(=O)C>O1CCCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:1][C@@H:2]2[CH2:6][CH2:5][CH2:4][C@H:3]2[CH2:7][OH:8])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 13514421rel-(1R,2R)-2-Aminocyclopentanemethanol

Product 1

HCID 594977994-chloro-N-(trans-2-hydroxymethylcyclopentyl)benzenesulfonamideYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-2-aminocyclopentylmethanol (prepared according to LaPlae et al., J. Org. Chem., 66:5629-5632 (2001)) (1.05 g, 7.5 mmol) and triethylamine (1.25 mL, 9.0 mmol) in 25 mL tetrahydrofuran was added 4-chlorobenzenesulfonyl chloride (1.90 g, 9.0 mmol). The reaction was stirred at room temperature for 2 h, then diluted into 100 mL ethyl acetate and extracted with brine (50 mL). The organic layer was concentrated and purified by flash chromatography on a 40 g silica gel column using a gradient of 20 to 80% ethyl acetate in hexane over 30 min to give 4-chloro-N-(trans-2-hydroxymethylcyclopentyl)benzenesulfonamide (1.61 g, 74%). 1H NMR (400 MHz, CDCl3) δ ppm 7.77-7.85 (2H, m), 7.42-7.52 (2H, m), 5.10 (1H, d, J=6.29 Hz), 3.70 (1H, ddd, J=10.64, 5.22, 5.04 Hz), 3.41-3.53 (1H, m), 3.21-3.33 (1H, m), 1.70-1.98 (4H, m), 1.44-1.68 (3H, m), 1.31-1.44 (1H, m). LC/MS R.T.=2.33 min; [M+H]+=290.06.

Workup

  1. extractionextracted with brine (50 mL)
  2. concentrationThe organic layer was concentrated
  3. custompurified by flash chromatography on a 40 g silica gel column
  4. customover 30 min

Sources & evidence

ORD record
ord-24326df1c156444b875a6e8beee2d039
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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