Réaction #2254212

ord-dd929053cec843bdb7692bdb88299df8

Équation de réaction

N#CC[C@@]1(c2ccc(F)cc2)CCOC2(CCCC2)C1
2-[(9R)-9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LAH
NCC[C@@]1(c2ccc(F)cc2)CCOC2(CCCC2)C1
2-[(9R)-9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]ethan-1-amine

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreAfter 2 h the reaction was quenched with 1 ml H2O, 0.2 ml 15% NaOH
  2. 2
    ExtractionThe reaction mixture was extracted with Et2O (3×30 ml)
  3. 3
    Autredried over NA2SO4
  4. 4
    Concentrationconcentrated

Mode opératoire

To a solution of 2-[(9R)-9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile (500 mg, 1.8 mmol) in anhydrous ether (30 ml) at 0° C. was added dropwise LAH (1.0 M in Et2O, 3.7 ml, 3.7 mmol). The reaction was then warmed up to room temperature. After 2 h the reaction was quenched with 1 ml H2O, 0.2 ml 15% NaOH and then 1 ml H2O. The reaction mixture was extracted with Et2O (3×30 ml), dried over NA2SO4 and concentrated to give 2-[(9R)-9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]ethan-1-amine as an yellow oil, which used without further purification (500 mg, 100%, m/z 277.2 [M+H]+ observed).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09044469B2uspto-grants-2015_06