Chloroform → (R/S)-3-(Allylamino)-1-(4-bromo-5-isoquinolinesulfony)pyrrolidine

HRID 1436024Notes

Reaction equation

HRID 1436024 reaction equation
Cl.[NH2:2][CH:3]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[C:12]3[C:13]([Br:21])=[CH:14][N:15]=[CH:16][C:17]=3[CH:18]=[CH:19][CH:20]=2)(=[O:10])=[O:9])[CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[CH:29]=[CH2:30].C(Cl)(Cl)Cl>CN(C)C=O.[Cl-].[Na+].O>[CH2:30]([NH:2][CH:3]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[C:12]3[C:13]([Br:21])=[CH:14][N:15]=[CH:16][C:17]=3[CH:18]=[CH:19][CH:20]=2)(=[O:10])=[O:9])[CH2:4]1)[CH:29]=[CH2:28]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 672429033-Amino-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine hydrochloride

Product 1

HCID 67243931(R/S)-3-(Allylamino)-1-(4-bromo-5-isoquinolinesulfony)pyrrolidine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 3-amino-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine hydrochloride (65 mg) obtained in Example 1 and potassium carbonate (148 mg, Wako Pure Chemical Industries) in N,N-dimethylformamide (5 ml) is added with allyl bromide (0.453 ml, Tokyo Kasei Kogyo), and the mixture is stirred at 50° C. for 12 hours. The reaction mixture is cooled to room temperature, and then added with saturated brine (10 ml) and chloroform (10 ml), and the organic layer is separated. The aqueous layer is extracted 3 times with chloroform (10 ml for each time), and the combined organic layer is washed twice with saturated brine (20 ml for each time). The organic layer is dried over anhydrous magnesium sulfate, and then the solvent is evaporated under reduced pressure. The residue is purified by silica gel chromatography (chloroform:methanol=30:1) to obtain the title compound (30 mg (predictive yield)).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe organic layer is separated
  3. extractionThe aqueous layer is extracted 3 times with chloroform (10 ml for each time), and the combined organic layer
  4. washis washed twice with saturated brine (20 ml for each time)
  5. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. customThe residue is purified by silica gel chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-71fb9f5a4d2b44bdb91670e161149d53
Source dataset
uspto-grants-2009_11
Patent number
US07618984B2

Reaction notes

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