Ethyl Bromide → (R)-1-ethyl-3-(3-fluorobenzyl)pyrrolidine

HRID 927981Notes

Reaction equation

HRID 927981 reaction equation
[CH2:1](Br)[CH3:2].[F:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[CH2:8][C@@H:9]1[CH2:13][CH2:12][NH:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[CH2:1]([N:11]1[CH2:12][CH2:13][C@@H:9]([CH2:8][C:7]2[CH:14]=[CH:15][CH:16]=[C:5]([F:4])[CH:6]=2)[CH2:10]1)[CH3:2]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 863184933-(R)-(3-fluorobenzyl)pyrrolidine2×

Product 1

HCID 70983712(R)-1-ethyl-3-(3-fluorobenzyl)pyrrolidineYield 57.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl bromide (0.22 g) was added to a suspension of 3-(R)-(3-fluorobenzyl)pyrrolidine (Intermediate 98, 0.36 g) and potassium carbonate (0.55 g) in acetonitrile and the mixture was stirred at room temperature for 2.5 hours. The mixture was diluted with ethyl acetate, filtered and the filtrate was evaporated to dryness. The residue was triturated with DCM, the solvent was decanted off and evaporated to dryness to give (R)-1-ethyl-3-(3-fluorobenzyl)pyrrolidine (0.24 g) as an oil.

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was triturated with DCM
  4. customthe solvent was decanted off
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-99498eca04b14674ac15b36eef5d47f7
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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