Ammonium Chloride → HCID 178430664, compound

HRID 367311Notes

Reaction equation

HRID 367311 reaction equation
[NH2:1][NH:2][C:3]([NH:5][CH2:6][C:7]1([CH3:28])[CH2:11][C:10]2[C:12]([C:24]([CH3:27])([CH3:26])[CH3:25])=[C:13]([O:20]C(=O)C)[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:15][C:9]=2[O:8]1)=[NH:4].[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[NH2:1][NH:2][C:3]([NH:5][CH2:6][C:7]1([CH3:28])[CH2:11][C:10]2[C:12]([C:24]([CH3:27])([CH3:26])[CH3:25])=[C:13]([OH:20])[C:14]([C:16]([CH3:17])([CH3:18])[CH3:19])=[CH:15][C:9]=2[O:8]1)=[NH:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 178475393HCID 178475393, compound

Product 1

HCID 178430664HCID 178430664, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, 0.98 g of 1-amino-3-[(5-acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]guanidine was dissolved in 50 ml of toluene. To the solution was added 10 ml of diisobutyl aluminum hydride (1.0 M in toluene) and the mixture was stirred at room temperature for 1 hour. After reaction, a saturated aqueous ammonium chloride solution was added and insoluble matters were filtered off on Celite. The filtrate was extracted with ethyl acetate and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography eluting with chloroform containing 10% methanol to give 0.32 g of 1-amino-3-[(4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]guanidine as a white crystal (yield 37%).

Workup

  1. customAfter reaction
  2. filtrationinsoluble matters were filtered off on Celite
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography
  8. washeluting with chloroform containing 10% methanol

Sources & evidence

ORD record
ord-292d3a22c74e4b62b891b756023efcca
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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