Benzenesulfonyl chloride → HCID 12132429, compound

HRID 2307397Notes

Reaction equation

HRID 2307397 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][C@@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[C:26]1([S:32](Cl)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[C:26]1([S:32]([N:1]2[C:9]3[C:4](=[C:5]([O:10][CH2:11][C@@H:12]4[CH2:16][CH2:15][CH2:14][N:13]4[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 12132428HCID 12132428, compound

Product 1

HCID 12132429HCID 12132429, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of t-butyl (2S)-2-[(1H-indol-4-yloxy)methyl]-1-pyrrolidinecarboxylate (1.23 g, 3.89 mmol) in THF is treated with sodium hydride (0.17 g, 60% in mineral oil, 4.28 mmol) under nitrogen at room temperature, stirred for 30 minutes, treated with benzenesulfonyl chloride (0.55 mL, 4.28 mmol), stirred at room temperature for 22 h, quenched with ice-water and diluted with EtOAc. The organic phase is separated, washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (siliga gel, EtOAc/hexanes, 2/8) to afford the title compound as an off-white foam, 1.21 g, mp 48-50° C., identified by NMR and mass spectral analyses.

Workup

  1. stirringstirred at room temperature for 22 h
  2. customquenched with ice-water
  3. additiondiluted with EtOAc
  4. customThe organic phase is separated
  5. washwashed sequentially with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is purified by flash chromatography (siliga gel, EtOAc/hexanes, 2/8)

Sources & evidence

ORD record
ord-466ab3a9853e4bc68445865c59c4ff88
Source dataset
uspto-grants-2004_12
Patent number
US06831094B2

Reaction notes

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