(3R)-1-benzylpyrrolidin-3-amine → 3-[3-((R)-1-benzyl-pyrrolidin-3-yl)-ureido]-benzenesulfonamide

HRID 1882526Notes

Reaction equation

HRID 1882526 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH2:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([O:20][C:21](=O)[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([S:29](=[O:32])(=[O:31])[NH2:30])[CH:24]=2)C=CC=CC=1>CO>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:21](=[O:20])[NH:22][C:23]2[CH:24]=[C:25]([S:29]([NH2:30])(=[O:32])=[O:31])[CH:26]=[CH:27][CH:28]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1519354(3R)-1-benzylpyrrolidin-3-amineHCID 39870106129513-94-6

Product 1

HCID 666311133-[3-((R)-1-benzyl-pyrrolidin-3-yl)-ureido]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (R)-N-benzyl-3-aminopyrrolidine (14.9 g, 0.084 mol) in methanol (100 mL) is added to a suspension of (3-sulfamoyl-phenyl)-carbamic acid phenyl ester (25 g, 0.084 mol). The resulting pale orange solution is stirred at mild reflux (DrySyn @ 80° C.) for two hours, then allowed to cool to room temperature, before the volatile components are removed under reduced pressure. The orange syrup is purified by flash column chromatography (silica; DCM/methanol 10:1) to give a beige foamed solid.

Workup

  1. temperatureto cool to room temperature, before the volatile components
  2. customare removed under reduced pressure
  3. customThe orange syrup is purified by flash column chromatography (silica; DCM/methanol 10:1)
  4. customto give

Sources & evidence

ORD record
ord-e6e8fcd2a704469b8b34eab6a5c24c71
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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