Furfural → (R/S)-3-(2-Furylmethyl)amino 1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine

HRID 1436023Notes

Reaction equation

HRID 1436023 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.[CH:22](=O)[C:23]1[O:27][CH:26]=[CH:25][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl.C(N(CC)CC)C>[O:27]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:22][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

Participants

7

Reactant 4

HCID 7362FurfuralHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 672429033-Amino-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine hydrochloride

Product 1

HCID 67244220(R/S)-3-(2-Furylmethyl)amino 1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidineYield 27.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 3-amino-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine hydrochloride (172 mg) obtained in Example 1 in 1,2-dichloroethane (10 ml) is added with triethylamine (0.28 ml, Wako Pure Chemical Industries), and then with furfural (42 mg, Aldrich), and the mixture is stirred at room temperature for 30 minutes, then added with sodium triacetoxyborohydride (170 mg, Aldrich), and further stirred at room temperature for 30 hours. The reaction mixture is added with saturated aqueous sodium hydrogencarbonate (15 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 with saturated brine (30 ml). 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 (52 mg (predictive yield)).

Workup

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

Sources & evidence

ORD record
ord-f133c00155d644fb994730953c4ca1d9
Source dataset
uspto-grants-2009_11
Patent number
US07618984B2

Reaction notes

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