4-Chlorobenzenesulfonyl chloride → HCID 69471349, compound

HRID 853778Notes

Reaction equation

HRID 853778 reaction equation
[C:1]1([C@H:7]2[CH2:11][CH2:10][C@@H:9]([CH2:12][O:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(Cl)CCl.C(Cl)Cl>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([N:8]2[C@H:9]([CH2:12][O:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10][CH2:11][C@@H:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 69472417HCID 69472417, compound

Product 1

HCID 69471349HCID 69471349, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (2R,5S)-2-phenyl-5-trimethylsilanyloxymethyl-pyrrolidine (0.98 g, 3.9 mmol) in ClCH2CH2Cl (5 mL) was added 1.9 mL (13.7 mmol, 3.5 eq) of Et3N and 1.45 g (6.86 mmol, 1.8 eq) of 4-chlorobenzenesulfonyl chloride. The mixture was heated at 70° C. for 16 hr. After cooling to room temperature, the mixture was diluted with CH2Cl2 (20 mL), washed with water (10 mL), saturated brine (10 mL), dried (Na2SO4) and concentrated under vacuum. The crude product was chromatographed on silica gel (2% EtOAc/hexane) to give 0.78 g (46%) of (2R,5S)-1-(4-chloro-benzenesulfonyl)-2-phenyl-5-trimethylsilanyloxymethyl-pyrrolidine as a yellow gum.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (10 mL), saturated brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under vacuum
  5. customThe crude product was chromatographed on silica gel (2% EtOAc/hexane)

Sources & evidence

ORD record
ord-9da0e76414ca4085a212da2bb0dfdada
Source dataset
uspto-grants-2007_08
Patent number
US07256186B2

Reaction notes

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