Methanol → {2-[2-(Benzyloxy)-4,6-di-tert-butylphenyl]ethyl}amine

HRID 1173336Notes

Reaction equation

HRID 1173336 reaction equation
[BH4-].[Li+].Cl[Si](C)(C)C.[CH2:8]([O:15][C:16]1[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:19]=[C:18]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:17]=1[CH:30]=[CH:31][N+:32]([O-])=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CO>C1COCC1>[CH2:8]([O:15][C:16]1[CH:21]=[C:20]([C:22]([CH3:23])([CH3:25])[CH3:24])[CH:19]=[C:18]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:17]=1[CH2:30][CH2:31][NH2:32])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 687177311-(Benzyloxy)-3,5-di-tert-butyl-2-[2-nitrovinyl]benzene

Product 1

HCID 68714462{2-[2-(Benzyloxy)-4,6-di-tert-butylphenyl]ethyl}amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.0 g (4.59 mmol) of lithium borohydride in 3 mL THF was carefully added 1.3 mL (10.2 mmol) of chlorotrimethylsilane. The reaction mixture was stirred for 2 min and then a solution of 0.367 g (1.0 mmol) of 1-(benzyloxy)-3,5-di-tert-butyl-2-[2-nitrovinyl]benzene from Step B of Example 75 dissolved in 1.5 mL of anhydrous THF was slowly added. The resulting reaction mixture was stirred overnight at room temperature then cooled using an external ice water bath and 15 mL of methanol was slowly added. The resulting mixture was evaporated in vacuo, the residue was the treated with 20 mL of 5 N aqueous sodium hydroxide and then the reaction mixture was extracted with 5 times with 20 mL portions of CH2Cl2. The combined extracts were dried Na2SO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted initially with 5% MeCOH in CH2Cl2 followed by a 95/5/0.5 mixture of CH2Cl2-MeOH-conc. NH4OH. Combination of the purified fractions and evaporation in vacuo afforded the title compound.

Workup

  1. additionwas slowly added
  2. customThe resulting reaction mixture
  3. stirringwas stirred overnight at room temperature
  4. temperaturethen cooled
  5. customThe resulting mixture was evaporated in vacuo
  6. additiontreated with 20 mL of 5 N aqueous sodium hydroxide
  7. extractionthe reaction mixture was extracted with 5 times with 20 mL portions of CH2Cl2
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was purified on a silica gel flash chromatography column
  11. washeluted initially with 5% MeCOH in CH2Cl2
  12. additionfollowed by a 95/5/0.5 mixture of CH2Cl2-MeOH-conc
  13. customCombination of the purified fractions and evaporation in vacuo

Sources & evidence

ORD record
ord-64dd1cfd35a94a0ca64484acf86845e4
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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