Methanol → 3,5-Di-tert-butyl-2-[2-(cyclohexylamino)ethyl]phenol

HRID 733311Notes

Reaction equation

HRID 733311 reaction equation
[BH4-].[Li+].Cl[Si](C)(C)C.C([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)C1C=CC=CC=1.CO>C1COCC1>[C:26]([C:18]1[C:17]([CH2:30][CH2:31][NH:32][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:16]([OH:15])[CH:21]=[C:20]([C:22]([CH3:24])([CH3:23])[CH3:25])[CH:19]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

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

Product 1

HCID 103820523,5-Di-tert-butyl-2-[2-(cyclohexylamino)ethyl]phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.10 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% MeOH 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. dry with materialThe combined extracts were dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe residue was purified on a silica gel flash chromatography column
  12. washeluted initially with 5% MeOH in CH2Cl2
  13. additionfollowed by a 95/5/0.5 mixture of CH2Cl2—MeOH-conc
  14. customCombination of the purified fractions and evaporation in vacuo

Sources & evidence

ORD record
ord-3135e75b698c46cb994ba355458fbf0b
Source dataset
uspto-grants-2009_09
Patent number
US07589127B2

Reaction notes

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