Oxalic Acid → HCID 25143956, compound

HRID 1931842Notes

Reaction equation

HRID 1931842 reaction equation
[F: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:15](#N)[CH3:16].[C:18](=O)([O-])[O-:19].[K+].[K+].C(O)(=O)C(O)=O>CO>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][N:11]([CH2:16][CH2:15][O:19][CH3:18])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 63585886HCID 63585886, compound

Product 1

HCID 25143956HCID 25143956, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Preparation according to Example 51: Enantiomer E1 of 3-(3,5-difluorophenyl)-pyrrolidin-3-ol (0.18 g, 0.92 mmol), acetonitrile (6 mL), potassium carbonate (0.25 g, 1.84 mmol) and 2-bromo ethyl methyl eter (0.09 mL, 0.92 mmol). Flash chromatography on silica gel (ethyl acetate/methanol, 10:1). Yield: 0.118 g. [α]D=+22.3° (methanol). The amine was converted to the oxalic acid salt and recrystallized from methanol/diisopropyl ether: M.p. 131-132° C.; MS m/z (relative intensity, 70 eV) 257 (M+, 2), 212 (bp), 182 (52), 213 (13), 127 (13), 58 (9).

Workup

  1. customPreparation
  2. customrecrystallized from methanol/diisopropyl ether

Sources & evidence

ORD record
ord-584d5bc7e2b345948f857abac3f560bd
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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