Triphenylphosphine → 3-(2,2-dimethyl-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester

HRID 2089485Notes

Reaction equation

HRID 2089485 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1O.[NH:13]1[CH:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[N:15]=[CH:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C([O-])(O)=O.[Na+].C(OCC)(=O)C>[CH3:21][O:20][C:18]([C:16]1[N:15]([CH:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:10][C:2]2([CH3:12])[CH3:1])[CH:14]=[N:13][CH:17]=1)=[O:19]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 109427712,3-Dihydro-2,2-dimethyl-1H-inden-1-olHCID 178418785HCID 178418785, compound

Product 1

HCID 218730963-(2,2-dimethyl-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,2-dimethyl-indan-1-ol (3.5 g, 21.6 mmol) in THF (160 mL) is added methyl 4-imidazolecarboxylate (CAS#17325-26-7, 4.1 g, 32.3 mmol), and triphenylphosphine (9.09 g, 34.5 mmol). The reaction is cooled to 0° C. and diisopropyl azodicarboxylate (6.67 mL, 34.5 mmol) is added. After one hour the reaction is diluted with saturated aqueous NaHCO3 and ethyl acetate. The layers are separated and the organic layer is dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0:1 to 1:1) to provide 3-(2,2-dimethyl-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester. HRMS: (ESI) m/z 271.1440 [(M+H)+: Calcd for C16H19N2O2: 271.1447]; 1H NMR (400 MHz, CDCl3) δ ppm 2.60-3.08 (m, 2 H), 3.92 (s, 3 H), 6.25 (s, 1 H), 7.03 (s, 1 H), 7.15-7.46 (m, 4 H), 7.80 (d, J=1.0 Hz, 1 H). The HCl salt of the title compound can be prepared by dissolution in diethyl ether followed by treatment with an excess of 1N HCl in diethyl ether. The resulting heterogeneous solution is concentrated to furnish the HCl salt of 3-(2,2-dimethyl-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester.

Workup

  1. customThe layers are separated
  2. dry with materialthe organic layer is dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0:1 to 1:1)

Sources & evidence

ORD record
ord-b51169732aee4f3d871c962b82bc889a
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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