Sodium Fluoride → HCID 59199358, compound

HRID 2089516Notes

Reaction equation

HRID 2089516 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH3:20])([CH3:19])[CH2:11]2)[CH:7]=[N:8][CH:9]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[F-].[Na+]>C1COCC1.O>[CH3:19][C:12]1([CH3:20])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([N:6]2[C:5]([CH2:3][OH:2])=[CH:9][N:8]=[CH:7]2)[CH2:11]1

Participants

6

Reactant 3

HCID 5235Sodium FluorideHCID 21226445Aluminium lithium hydrideHCID 59199378HCID 59199378, compound

Product 1

HCID 59199358HCID 59199358, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3,3-dimethyl-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester (1.31 g, 4.85 mmol), which can be prepared as described in Example 2, in THF (405 mL) at 0° C. is added LiAlH4 (220 mg, 5.6 mmol). The reaction is permitted to stir at room temperature for 2 hours at which time the reaction is cooled to 0° C., charged with sodium fluoride (205 mg, 4.88 mmol), and diluted with water. The reaction is brought to room temperature and stirred overnight. The reaction is then filtered and the eluent is extracted three times with ethyl acetate. The combined organic extracts are dried with Na2SO4, filtered and concentrated. The resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 0:1 to 1:10) to provide 3-(3,3-dimethyl-indan-1-yl)-3H-imidazol-4-yl]-methanol; MS: (ESI) m/z 243.1 (M+H)+.

Workup

  1. temperatureis cooled to 0° C.
  2. customis brought to room temperature
  3. stirringstirred overnight
  4. filtrationThe reaction is then filtered
  5. extractionthe eluent is extracted three times with ethyl acetate
  6. dry with materialThe combined organic extracts are dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 0:1 to 1:10)
  10. customto provide 3-(3,3-dimethyl-indan-1-yl)-3H-imidazol-4-yl]-methanol

Sources & evidence

ORD record
ord-4ce219cb87b24081bf878227a42f82e5
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

Loading…