Oxalic Acid → (+)-1-Allyl-3-(2,3-difluorophenyl)pyrrolidin-3-OL

HRID 1931849Notes

Reaction equation

HRID 1931849 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:15](=O)([O-])[O-].[K+].[K+].[C:21](O)(=O)[C:22](O)=O>C(#N)C>[CH2:15]([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)[CH:21]=[CH2:22]

Participants

5

Reactant 3

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

Product 1

HCID 25143817(+)-1-Allyl-3-(2,3-difluorophenyl)pyrrolidin-3-OL

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, 0.75 mmol), acetonitrile (6 mL), potassium carbonate (0.208 g, 1.5 mmol) allyl bromide (0.065 mL, 0.76 mmol). Flash chromatography on silica gel (Ethyl acetate/methanol, 10:1). Yield 0.1 g. [α]D=+23.4°; The amine was converted to the oxalic acid salt and recrystallized from ethanol/diethyl ether/diisopropyl ether; M.p. 119-120° C.; MS m/z (relative intensity, 70 eV) 239 (M+, 13), 83 (bp), 141 (41), 82 (39), 198 (35), 84 (32).

Workup

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

Sources & evidence

ORD record
ord-ee8de8f7fda64eba9465be07670374f9
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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