Diisobutylaluminum hydride → 1-Cyclobutyl-4-(3-ethyl-5-methyl-2-naphthalen-1-yl-3H-imidazol-4-ylmethyl)-piperazine

HRID 12472Notes

Reaction equation

HRID 12472 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11]([C:13]3[N:14]([CH2:29][CH3:30])[C:15]([C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:22]=[CH:21][CH:20]=4)=[N:16][C:17]=3[CH3:18])=O)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.CC(C[AlH]CC(C)C)C>C1COCC1>[CH:1]1([N:5]2[CH2:6][CH2:7][N:8]([CH2:11][C:13]3[N:14]([CH2:29][CH3:30])[C:15]([C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:22]=[CH:21][CH:20]=4)=[N:16][C:17]=3[CH3:18])[CH2:9][CH2:10]2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 59338300HCID 59338300, compound

Product 1

HCID 593385021-Cyclobutyl-4-(3-ethyl-5-methyl-2-naphthalen-1-yl-3H-imidazol-4-ylmethyl)-piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-cyclobutyl-piperazin-1-yl)-(3-ethyl-5-methyl-2-naphthalen-1-yl-3H-imidazol-4-yl)-methanone (40 mg) in THF (1 ml) is added DIBAL-H (0.25 ml, 1.5 M in toluene) at 0° C. The resulting solution is stirred at rt for 2 hr, and then quenched with brine. The THF layer is separated, evaporated and purified by column (2% Et3N, 3% MeOH in EtOAc) to afford the title compound. LCMS 389.5 (M+1). NMR (CDCl3) δ ppm 1.05 (t, 3H), 1.63-2.05 (m, 9H), 2.29 (s, 3H), 2.35-2.56 (m, 5H), 2.74 (m, 1H), 3.52 (s, 2H), 3.82 (q, 2H), 7.42-7.60 (m, 5H), 7.87-7.94 (m, 2H).

Workup

  1. customquenched with brine
  2. customThe THF layer is separated
  3. customevaporated
  4. custompurified by column (2% Et3N, 3% MeOH in EtOAc)

Sources & evidence

ORD record
ord-80481d022c79468f9dd37c5cace1fcb4
Source dataset
uspto-grants-2010_06
Patent number
US07728009B1

Reaction notes

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