Methanol → HCID 22872574, compound

HRID 1779995Notes

Reaction equation

HRID 1779995 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C@H:8]([C@@H:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH2:9][N:10]=[N+]=[N-].CO>C1COCC1>[CH3:7][C@H:8]([C@@H:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:18])[CH3:19])[CH2:9][NH2:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 21226445Aluminium lithium hydrideHCID 22872575HCID 22872575, compound

Product 1

HCID 22872574HCID 22872574, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6.3 mL (6.3 mmol) of 1M lithium aluminum hydride in THF was added dropwise to a solution of 2(R),3(S),7-trimethyl-1-azido-6-octene in 10 mL of THF at 0° C. The reaction mixture was heated to reflux 18 hrs. After cooling in ice bath, ~1 mL of methanol was added dropwise cautiously. After the effervescence stopped, the reaction mixture was concentrated to 30% of the volume and 1N solution of potassium sodium tartrate was added. After stirring 15 mins, the reaction mixture was extracted with ethyl acetate. The combined ethyl acetate layers were dried over anhydrous magnesium sulfate and the solvent was removed to give 399 mg of the desired amine as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux 18 hrs
  3. temperatureAfter cooling in ice bath
  4. concentrationthe reaction mixture was concentrated to 30% of the volume and 1N solution of potassium sodium tartrate
  5. additionwas added
  6. extractionthe reaction mixture was extracted with ethyl acetate
  7. dry with materialThe combined ethyl acetate layers were dried over anhydrous magnesium sulfate
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-26095c0786d3403c800242f0dbde6783
Source dataset
uspto-grants-1997_05
Patent number
US05629322

Reaction notes

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