Oxalic Acid → HCID 25143955, compound

HRID 1931843Notes

Reaction equation

HRID 1931843 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+].[CH2:21](Br)[CH:22]=[CH2:23].C(O)(=O)C(O)=O>CO.C(#N)C>[CH2:23]([N:11]1[CH2:12][CH2:13][C:9]([C:4]2[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=2)([OH:14])[CH2:10]1)[CH:22]=[CH2:21]

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 63585886HCID 63585886, compound

Product 1

HCID 25143955HCID 25143955, 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) and allyl bromide (0.077 mL, 0.92 mmol). Flash chromatography on silica gel (ethyl acetate/methanol, 10:1). Yield: 0.1 g. [α]D=+22.4° (methanol). The amine was converted to the oxalic acid salt and recrystallized from methanol/diisopropyl ether: M.p. 104-105° C.; MS m/z (relative intensity, 70 eV) 239 (M+, 40), 83 (bp), 198 (84), 82 (13), 14 (33), 127 (31).

Workup

  1. customPreparation
  2. customrecrystallized from methanol/diisopropyl ether

Sources & evidence

ORD record
ord-0b7a68095b4a4971812eeb53f3b3e0ee
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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