Sodium Hydroxide → (R)-1-ethyl-2-[2-(3-fluorophenyl)ethyl]pyrrolidine

HRID 928084Notes

Reaction equation

HRID 928084 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15](=O)[CH3:16])[CH:5]=[CH:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S(=O)(=O)(O)[O-].[Na+]>C1COCC1.O>[CH2:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[CH3:16]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 516919Sodium BisulfateHCID 21226445Aluminium lithium hydrideHCID 709837131-{(R)-2-[2-(3-fluorophenyl)ethyl]pyrrolidin-1-yl}ethanone2×

Product 1

HCID 71007002(R)-1-ethyl-2-[2-(3-fluorophenyl)ethyl]pyrrolidineYield 90.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-{(R)-2-[2-(3-fluorophenyl)ethyl]pyrrolidin-1-yl}ethanone (Intermediate 232, 0.48 g) in THF (20 mL) was cooled to 0° C. and treated with a solution of lithium aluminum hydride (2M in THF, 3.6 mL) under an atmosphere of nitrogen. The resultant mixture was allowed to warm to room temperature before heating to 60° C. overnight. The mixture was cooled to 0° C. and treated with water (0.35 ml), 4N sodium hydroxide solution (0.35 ml) and further water (0.9 ml). Sodium bisulphate powder was added to the suspension and the slurry was filtered through Celite and the filtrate was evaporated to dryness to give (R)-1-ethyl-2-[2-(3-fluoro-phenyl)ethyl]pyrrolidine (0.41 g) as an oil.

Workup

  1. temperaturebefore heating to 60° C. overnight
  2. temperatureThe mixture was cooled to 0° C.
  3. filtrationthe slurry was filtered through Celite
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-27b36a7653544f2b841fe4873afeded9
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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