Oxalic Acid → HCID 25143957, compound

HRID 1931841Notes

Reaction equation

HRID 1931841 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(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH:23]([CH3:25])[CH3:24].C(O)(=O)C(O)=O>CO.C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][N:11]([CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 63585886HCID 63585886, compound

Product 1

HCID 25143957HCID 25143957, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

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), 1-bromo-2-methylpropane (0.1 mL, 0.92 mmol). Flash chromatography on silica gel (ethyl acetate/methanol, 9:1). Yield: 0.18 g. [α]D=+22.6° (methanol). The amine was converted to the oxalic acid salt and recrystallized from methanol/diisopropyl ether: M.p. 164-165° C.; MS m/z (relative intensity, 70 eV) 255 (M+, 2), 212 (bp), 182 (46), 213 (12), 127 (8), 98 (6) 1-bromo-2-methylpropane.

Workup

  1. customPreparation
  2. customrecrystallized from methanol/diisopropyl ether

Sources & evidence

ORD record
ord-75794111d9e24b41a9afcc0623673e29
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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