Pyrrolidine → 2-Hydroxy-5-chlorobenzene sulfonyl pyrrolidine

HRID 926981Notes

Reaction equation

HRID 926981 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>C(Cl)(Cl)Cl>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 3043845-Chloro-2-hydroxybenzene-1-sulfonyl chloride

Product 1

HCID 694041512-Hydroxy-5-chlorobenzene sulfonyl pyrrolidineYield 77.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of the product of Example 44A (2.16 g, 9.51 mmol) in CHCl3 (8 mL) was added, with ice cooling, pyrrolidine (4.05 g, 57.04 mmol). The mixture was stirred at 25° C. for 2 hrs, then concentrated in vacuo. The residue was dissolved in toluene, washed with HCl and water, dried (Na2SO4) and concentrated. The resulting oil was crystallized from hexane and chromatographed (CH2Cl2) to yield the title compound (1.92 g), m.p. 101-102° C.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in toluene
  3. washwashed with HCl and water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe resulting oil was crystallized from hexane
  7. customchromatographed (CH2Cl2)

Sources & evidence

ORD record
ord-10aa4a7be5e14c8eb50c8ad033382a2d
Source dataset
uspto-grants-2016_03
Patent number
US09290444B2

Reaction notes

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