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

HRID 1931850Notes

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+].[C:21](O)(=O)[C:22](O)=O.[C:27](#N)[CH3:28]>>[CH:21]1([CH2:22][N:11]2[CH2:12][CH2:13][C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])([OH:14])[CH2:10]2)[CH2:28][CH2:27]1

Participants

Reactant 4

HCID 971Oxalic Acid

HCID 6342Acetonitrile

HCID 11430Potassium Carbonate

HCID 639883833-(2,3-Difluorophenyl)pyrrolidin-3-ol

Product 1

HCID 25143959(+)-1-(Cyclopropylmethyl)-3-(2,3-difluorophenyl)pyrrolidin-3-OL

Procedure

Preparation according to Example 51. Enantiomer E1 of 3-(2,3-difluorophenyl)-pyrrolidin-3-ol (0.11 g, 0.55 mmol), acetonitrile (6 mL), potassium carbonate (0.140 g, 1 mmol) cyclopropylmethyl bromide (0.05 mL, 0.51 mmol). Flash chromatography on silica gel (Ethyl acetate/methanol, 10:1). Yield: 0.045 g. [α]D=+12.5°; The amine was converted to the oxalic acid salt and recrystallized from ethanol/diethyl ether/diisopropyl ether; Mp. 170-171° C.; MS m/z (relative intensity, 70 eV) 253 (M+, 27), 96 (bp), 97 (60), 55 (44), 141 (32), 98 (2).

Workup

customPreparation
customrecrystallized from ethanol/diethyl ether/diisopropyl ether

Sources & evidence

ORD record: ord-ac9ea7ec6f7249138cc90485d76878b5
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188301B2

Reaction notes

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