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Water → 4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]phenylethylsulfone

HRID 1811633
Notes
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Reaction equation

HRID 1811633 reaction equation
Cl.Cl.[C:3]1([C@H:13]([NH:15][C@H:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)[CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.F[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][S:30]([CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38](F)=[CH:37][CH:36]=2)(=[O:32])=[O:31])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C(Cl)(Cl)Cl>[C:3]1([C@H:13]([NH:15][C@H:16]2[CH2:20][CH2:19][N:18]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][S:30]([CH2:33][CH2:34][C:35]4[CH:40]=[CH:39][C:38]([N:18]5[CH2:19][CH2:20][C@H:16]([NH:15][C@@H:13]([C:3]6[C:12]7[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=7)[CH:6]=[CH:5][CH:4]=6)[CH3:14])[CH2:17]5)=[CH:37][CH:36]=4)(=[O:32])=[O:31])=[CH:24][CH:23]=3)[CH2:17]2)[CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 534437264-FluorophenylethylsulfoneHCID 67408696(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidine dihydrochloride

Product 1

HCID 674070244-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]phenylethylsulfoneYield 73.7%

Reagents, catalysts & solvents

2
HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 150 mg of (S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidine dihydrochloride and 108 mg of 4-fluorophenylethylsulfone in 2 ml of DMSO was added 263 mg of potassium carbonate, and the reaction mixture was stirred at 130° C. for 1 day. To the reaction mixture was added water and chloroform, the mixture was stirred and the liquids were separated. The organic layer was dried and evaporated, and then, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=80:20→40:60) to obtain 132.5 mg of 4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]phenylethylsulfone.

Workup

  1. stirringthe mixture was stirred
  2. customthe liquids were separated
  3. customThe organic layer was dried
  4. customevaporated
  5. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=80:20→40:60)

Sources & evidence

ORD record
ord-fa54a85ba8734cb3b1c5902e5f364a86
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362274B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes