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

HRID 2425378Notes

Reaction equation

HRID 2425378 reaction equation
Cl.[NH2:2][C@H: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][C@H: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 67244372(S)-3-amino-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine hydrochloride

Product 1

HCID 16223986(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 (S)-3-amino-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine hydrochloride (172 mg) obtained in Example 1-1 in 1,2-dichloroethane (10 ml) was added with triethylamine (0.28 ml, Wako Pure Chemical Industries), and then with furfural (42 mg, Aldrich), and the mixture was 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 was added with saturated aqueous sodium hydrogencarbonate (15 ml), and the organic layer was separated. The aqueous layer was extracted 3 times with chloroform (10 ml for each time), and the combined organic layer was washed with saturated brine (30 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol=30:1) to obtain the title compound (52 mg).

Workup

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

Sources & evidence

ORD record
ord-e6f6201477724845a036b9dd614b3873
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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