Oxalic Acid → 3-(3-Chloro-5-fluorophenyl)-1-ethylpyrrolidin-3-ol

HRID 1931798Notes

Reaction equation

HRID 1931798 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].I[CH2:22][CH3:23].C(O)(=O)C(O)=O>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][N:11]([CH2:22][CH3:23])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 685156533-(3-Chloro-5-fluorophenyl)pyrrolidin-3-ol

Product 1

HCID 251457773-(3-Chloro-5-fluorophenyl)-1-ethylpyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 8: 3-(3-chloro-5-fluorophenyl)pyrrolidin-3-ol (0.30 g, 1.4 mmol), acetonitrile (20 mL), sodium carbonate (0.19 g, 3.5 mmol), iodoethane (0.22 g, 1.4 mmol). Yield: 0.17 g. The amine was converted to the oxalic acid salt and recrystallized from ethanol/diethyl ether/diisopropyl ether: M.p. 169-170° C.; MS m/z (relative intensity, 70 eV) 243 (M+, 8), 228 (7), 157 (7), 129 (7), 72 (30), 71 (bp).

Workup

  1. customPreparation
  2. customrecrystallized from ethanol/diethyl ether/diisopropyl ether

Sources & evidence

ORD record
ord-e99ca8bffa8041f4b6f9fc68a720969a
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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