Diisobutylaluminum hydride → 1-(4-tert-Butylphenyl)-3-(4-(hydroxymethyl)phenyl)imidazolidin-2-one

HRID 1710334Notes

Reaction equation

HRID 1710334 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:25]=[CH:24][C:19]([C:20](OC)=[O:21])=[CH:18][CH:17]=3)[C:12]2=[O:26])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C>ClCCl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:20][OH:21])=[CH:24][CH:25]=3)[C:12]2=[O:26])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 59456842Methyl 4-(3-(4-tert-butylphenyl)-2-oxoimidazolidin-1-yl)benzoate

Product 1

HCID 594568851-(4-tert-Butylphenyl)-3-(4-(hydroxymethyl)phenyl)imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl 4-(3-(4-tert-butylphenyl)-2-oxoimidazolidin-1-yl)benzoate (270 mg, 0.77 mmol) in dichloromethane (50 ml) at −78° C. was treated with ml of 1.0 M DIBAL solution in dichloromethane. The resulting solution was stirred cold for 2 hour, then quenched with ml of sat's Rochelle salt solution. The mixture was partitioned between 100 ml dichloromethane and 50 ml of 1 N NaOH. The organic layer was separated, dried and concentrated. The residue was purified on ISCO system (5% methanol in dichloromethane) to give a pure product as a white crystalline (113 mg, 35%): 1H NMR (400 MHz, CDCl3) δ 7.60 (d, 2H), 7.50 (d, 2H), 7.10 (m, 4H), 4.64 (s, 2H), 4.00 (s, 4H), 1.58 (s, 9H).

Workup

  1. customquenched with ml of sat's Rochelle salt solution
  2. customThe mixture was partitioned between 100 ml dichloromethane and 50 ml of 1 N NaOH
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified on ISCO system (5% methanol in dichloromethane)
  7. customto give a pure product as a white crystalline (113 mg, 35%)

Sources & evidence

ORD record
ord-a45fa349eb6944c2b13435c6cf4cffdd
Source dataset
uspto-grants-2010_09
Patent number
US07790707B2

Reaction notes

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