2-Methylimidazole → HCID 52934335, compound

HRID 2366948Notes

Reaction equation

HRID 2366948 reaction equation
[CH3:1][CH:2]([O:4][C:5](=[O:30])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](B3OC(C)(C)C(C)(C)O3)[CH:15]=2)[N:10]([C:26](=[O:28])[CH3:27])[C@@H:9]([CH3:29])[CH2:8]1)[CH3:3].[CH3:31][C:32]1[NH:33][CH:34]=[CH:35][N:36]=1>CO.[Cu-]=O>[CH3:3][CH:2]([O:4][C:5](=[O:30])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N:33]3[CH:34]=[CH:35][N:36]=[C:32]3[CH3:31])[CH:15]=2)[N:10]([C:26](=[O:28])[CH3:27])[C@@H:9]([CH3:29])[CH2:8]1)[CH3:1]

Participants

5

Reactant 2

HCID 127492-MethylimidazoleHCID 681853941-Methylethyl [(cis)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate

Product 1

HCID 52934335HCID 52934335, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of 1-methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 52) (500 mg, 1.2 mmol), 2-methylimidazole (99 mg, 1.2 mmol) and copper(I) oxide (10 mg, 0.126 mmol) in methanol (10 mL) was stirred in air at room temperature for 24 h. A further portion of copper(I) oxide (10 mg, 0.126 mmol) was added and stirring was continued for 48 h. The reaction mixture was then filtered through celite and most of the solvent were removed in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 5% MeOH in DCM) gave 1-methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(2-methyl-1H-imidazol-1-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (167 mg, 0.451 mmol, 37%) as a colourless foam.

Workup

  1. stirringstirring
  2. waitwas continued for 48 h
  3. filtrationThe reaction mixture was then filtered through celite and most of the solvent
  4. customwere removed in vacuo
  5. customPurification of the residue by flash chromatography on silica gel (gradient: 0 to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-e4f1d63ad2fa4fe59d35c7388215e670
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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