5-(p-Ethoxycarbonylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine → 5-(p-Hydroxymethylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

HRID 22552Notes

Reaction equation

HRID 22552 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[N:17]3[CH:18]=[N:19][CH:20]=[C:16]3[CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[OH:3][CH2:4][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[N:17]3[CH:18]=[N:19][CH:20]=[C:16]3[CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 136882135-(p-Ethoxycarbonylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridineHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 136882185-(p-Hydroxymethylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.40 g of 5-(p-ethoxycarbonylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine in 20 ml of methylene chloride is cooled to -70° under nitrogen and 4.0 ml of a 1.53M diisobutylaluminium hydride solution in toluene is added dropwise. The reaction mixture is allowed to warm to room temperature, quenched with 3.2 ml of methanol and 15 ml of water and filtered through Celite®. The layers are separated, the organic one is dried over sodium sulfate and evaporated to yield the title compound, m.p. 142°-145°.

Workup

  1. customquenched with 3.2 ml of methanol and 15 ml of water
  2. filtrationfiltered through Celite®
  3. customThe layers are separated
  4. dry with materialthe organic one is dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d495d66d4e7740828f5a729e517fa758
Source dataset
uspto-grants-1995_06
Patent number
US05428160

Reaction notes

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