5-Azido-5-(2-methoxyphenyl)-1-pentene → 5-Amino-5-(2-methoxyphenyl)-1-pentene

HRID 379513Notes

Reaction equation

HRID 379513 reaction equation
[N:1]([CH:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])[CH2:5][CH2:6][CH:7]=[CH2:8])=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[NH2:1][CH:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])[CH2:5][CH2:6][CH:7]=[CH2:8]

Participants

4

Reactant 2

HCID 158847225-Azido-5-(2-methoxyphenyl)-1-penteneHCID 21226445Aluminium lithium hydride

Product 1

HCID 158847235-Amino-5-(2-methoxyphenyl)-1-penteneYield 116.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 5-azido-5-(2-methoxyphenyl)-1-pentene (1.59 g. 7.33 mmol) in anhydrous ether (10 mL) at 0° C. was added to LiAlH4 in diethyl ether (1.0M, 7.33 mL) dropwise over a period of 20 minutes. The ice bath was removed and the reaction mixture was kept at room temperature for 25 minutes. The reaction solution was cooled to 0° C. to 40° C. and saturated Na2SO4 solution was added dropwise until no hydrogen gas was evolved. Anhydrous Na2SO4 was added followed by diethyl ether (70 mL), the resulting suspension was stirred at room temperature for 1 hour and the solution was then filtered through a pad of Celite™. The filtrate was evaporated to give the title compound (1.63 g) as a colorless oil, which was used for the Preparation 19 without purification. 1H NMR (CDCl3, 400 MHz) δ: 7.22 (2H), 6.93 (3H), 5.80 (1H), 4.92 (2H), 4.13 (1H), 3.82 (3H, OMe), 1.2-2.2 (6H).

Workup

  1. customThe ice bath was removed
  2. temperatureThe reaction solution was cooled to 0° C. to 40° C.
  3. additionsaturated Na2SO4 solution was added dropwise until no hydrogen gas
  4. additionAnhydrous Na2SO4 was added
  5. filtrationthe solution was then filtered through a pad of Celite™
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-64d23b1660304ca2a8d9223bb908bd45
Source dataset
uspto-grants-2001_10
Patent number
US06300316B1

Reaction notes

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