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

HRID 2382373Notes

Reaction equation

HRID 2382373 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-397265bda2344fad97ccab781732454c
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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