Water → HCID 15485725, compound

HRID 367297Notes

Reaction equation

HRID 367297 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:14][C:15]1[C:16]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:17][C:18]2[O:22][C:21]([CH2:24][NH2:25])([CH3:23])[CH2:20][C:19]=2[C:26]=1[C:27]([CH3:30])([CH3:29])[CH3:28])(=O)C.O>C1(C)C=CC=CC=1>[NH2:25][CH2:24][C:21]1([CH3:23])[CH2:20][C:19]2[C:26]([C:27]([CH3:30])([CH3:29])[CH3:28])=[C:15]([OH:14])[C:16]([C:31]([CH3:32])([CH3:33])[CH3:34])=[CH:17][C:18]=2[O:22]1

Participants

5

Reactant 3

HCID 962WaterHCID 154857245-Acetoxy-2-aminomethyl-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuranHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 15485725HCID 15485725, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Under a nitrogen atmosphere, 13.2 ml of 1M diisobutyl aluminum hydride solution in toluene was added dropwise to a solution of 1.0 g of 5-acetoxy-2-aminomethyl-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran in 30 ml of toluene at room temperature. After stirring at room temperature for 14 hours, the mixture was combined with water and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by recrystallization from a mixed solvent of ethyl acetate and hexane to give 0.62 g of 2-aminomethyl-4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran as a white crystal (yield 71%).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe resulting organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by recrystallization from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-e21e314ecfbe4830b613e3588806735e
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

Loading…