N,N'-Dimethylethylenediamine → (4S)-4-((tert-butyl(dimethyl)silyl)oxy)-1-(1-methyl-1H-pyrazol-3-yl)pyrrolidin-2-one

HRID 632747Notes

Reaction equation

HRID 632747 reaction equation
I[C:2]1[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=1.[Si:8]([O:15][C@@H:16]1[CH2:20][NH:19][C:18](=[O:21])[CH2:17]1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].CNCCNC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COC1CCCC1.C(OCC)(=O)C.[Cu]I>[Si:8]([O:15][C@@H:16]1[CH2:20][N:19]([C:2]2[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=2)[C:18](=[O:21])[CH2:17]1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 11074789(S)-4-(t-Butyldimethylsilyloxy)pyrrolidin-2-oneHCID 133340573-Iodo-1-methyl-1H-pyrazole

Product 1

HCID 131735442(4S)-4-((tert-butyl(dimethyl)silyl)oxy)-1-(1-methyl-1H-pyrazol-3-yl)pyrrolidin-2-oneYield 87%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 138539Cyclopentyl methyl etherSolvent

Procedure

A solution of 3-iodo-1-methyl-1H-pyrazole (1.7 g), (4S)-4-((tert-butyl(dimethyl)silyl)oxy)pyrrolidin-2-one (1.8 g), copper(I) iodide (315 mg), N1,N2-dimethylethane-1,2-diamine (0.36 mL) and tripotassium phosphate (3.5 g) in cyclopentyl methyl ether (34 mL) was stirred overnight at 120° C. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous ammonium chloride solution, water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.1 g).

Workup

  1. washwashed with saturated aqueous ammonium chloride solution, water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-eb51482e4a444d6c83eef074a2b72a5a
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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