Benzenesulfonyl chloride → HCID 69772541, compound

HRID 2307399Notes

Reaction equation

HRID 2307399 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]3C(OC(C)(C)C)=O)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CC(C)([O-])C.[K+].[C:30]1([S:36]([Cl:39])(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[ClH:39].[C:30]1([S:36]([N:1]2[C:9]3[C:4](=[C:5]([O:10][CH2:11][C@H:12]4[CH2:16][CH2:15][CH2:14][NH:13]4)[CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 12132432HCID 12132432, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 69772541HCID 69772541, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of t-butyl (2R)-2-[(1H-indol-4-yloxy)methyl]pyrrolidine-1-carboxylate (0.316 g, 1.0 mmol) in THF is treated with potassium t-butoxide (1.5 mL, 1.5 mmol, 1M in THF) at room temperature, stirred for 3 min, treated with benzenesulfonyl chloride (0.264 g, 1.5 mmol), stirred for 6 h under nitrogen at room temperature, quenched with IN aqueous HCl and 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 treated with HCl (1.5 mL, 1N in Et2O), heated at reflux temperature for 3 h, cooled to room temperature and filtered. The filtercake is air-dried to afford the title compound as an off-white solid, 0.24 g, mp 204-206° C., identified by NMR and mass spectral analyses.

Workup

  1. stirringstirred for 6 h under nitrogen at room temperature
  2. customquenched with IN aqueous HCl and 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. additionThe resultant residue is treated with HCl (1.5 mL, 1N in Et2O)
  9. temperatureheated
  10. temperatureat reflux temperature for 3 h
  11. filtrationfiltered
  12. customThe filtercake is air-dried

Sources & evidence

ORD record
ord-064f15d97ce047f4a1b3674ebe52eaa8
Source dataset
uspto-grants-2004_12
Patent number
US06831094B2

Reaction notes

Loading…