Sodium Hydroxide → HCID 18438570, compound

HRID 1643203Notes

Reaction equation

HRID 1643203 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]([CH2:36][C:37]3[CH:45]=[CH:44][C:40]4[O:41][CH2:42][O:43][C:39]=4[CH:38]=3)[C:12](=O)[CH2:13][C:14]3[N:15]([CH2:31][CH2:32][CH2:33][CH3:34])[C:16]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:17][C:18]=3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[O:41]1[C:40]2[CH:44]=[CH:45][C:37]([CH2:36][N:11]([CH2:10][C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)[CH2:12][CH2:13][C:14]3[N:15]([CH2:31][CH2:32][CH2:33][CH3:34])[C:16]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:17][C:18]=3[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:38][C:39]=2[O:43][CH2:42]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 18438569HCID 18438569, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18438570HCID 18438570, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N,N-bis-benzo[1,3]dioxol-5-ylmethyl-2-(3-butyl-2,5-diphenyl-3H-imidazol-4-yl)-acetamide (150 mg, 0.249 mmol) in tetrahydrofuran (25 mL) is cooled to 0° C. under a nitrogen atmosphere. Lithium aluminum hydride (95%, 30 mg, 0.747 mmol) is added in one portion and the reaction allowed to stir overnight warming to room temperature. Water (0.03 mL), sodium hydroxide (15% solution, 0.03 mL), and water (0.09 mL) are added and the reaction mixture is allowed to stir at 0° C. for 15 minutes. Magnesium sulfate is then added and the crude solution is filtered through a bed of Celite washing with 2% methanol in dichloromethane (100 mL). The crude sample is concentrated in vacuo and flash chromatographed on SiO2 using an eluent of dichloromethane:methanol 95:5 to afford bis-benzo[1,3]dioxol-5-ylmethyl-[2-(3-butyl-2,5-diphenyl-3H-imidazol-4-yl)-ethyl]-amine as a colorless syrup.

Workup

  1. stirringto stir at 0° C. for 15 minutes
  2. filtrationthe crude solution is filtered through a bed of Celite
  3. washwashing with 2% methanol in dichloromethane (100 mL)
  4. concentrationThe crude sample is concentrated in vacuo and flash
  5. customchromatographed on SiO2 using an eluent of dichloromethane:methanol 95:5

Sources & evidence

ORD record
ord-fbf0c3fa321e4950812c43aa8531036b
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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