Oxalic Acid → HCID 25143814, compound

HRID 1931846Notes

Reaction equation

HRID 1931846 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:14])[CH2:13][CH2:12][NH:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[CH2:22][CH2:23][CH3:24].C(O)(=O)C(O)=O>C(#N)C>[CH2:21]([N:11]1[CH2:12][CH2:13][C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])([OH:14])[CH2:10]1)[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 639883833-(2,3-Difluorophenyl)pyrrolidin-3-ol

Product 1

HCID 25143814HCID 25143814, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 51. Enantiomer E1 of 3-(2,3-difluorophenyl)-pyrrolidin-3-ol (0.15 g, 0.77 mmol), acetonitrile (6 mL), potassium carbonate (0.21 g, 1.55 mmol), n-butylbromid, (0.08 mL, 0.77). Flash chromatography on silica gel (Ethyl acetate/methanol, 7:1). Yield: 0.085 g. [α]D=+24.8°; The amine was converted to the oxalic acid salt and recrystallized from ethanol/diisopropyl ether; M.p. 157-158° C.; MS m/z (relative intensity, 70 eV) 255 (M+, 7), 212 (bp), 98 (52), 57 (40), 182 (37), 127 (16).

Workup

  1. customPreparation
  2. customrecrystallized from ethanol/diisopropyl ether

Sources & evidence

ORD record
ord-23ed72fc86e24cf591b7a7470623f3e9
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

Loading…