3-Pyrrolidinecarboxylic acid, 4-(2,4-difluorophenyl)-, methyl ester, (3S,4R)- synthesis

3synthesis methods

Product Name:3-Pyrrolidinecarboxylic acid, 4-(2,4-difluorophenyl)-, methyl ester, (3S,4R)-
CAS Number:923948-65-6
Molecular formula:C12H13F2NO2
Molecular Weight:241.23

TRANS-METHYL 1-BENZYL-4-(3,4-DIFLUOROPHENYL)PYRROLIDINE-3-CARBOXYLATE

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3-Pyrrolidinecarboxylic acid, 4-(2,4-difluorophenyl)-, methyl ester, (3S,4R)-

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Yield:923948-65-6 98%

Reaction Conditions:

with hydrogen;palladium(II) hydroxide/carbon in ethanol at 20; under 2587.76 Torr; for 24 h;

Steps:

8

Palladium hydroxide (20% on carbon, 1 g) was added to a solution of methyl(3S,4R)-1-benzyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate (from preparation 7) (10 g, 30 mmol) in ethanol (50 mL) at room temperature. The reaction mixture was hydrogenated at 345 kPa pressure (50 psi) for 24 hours and then filtered through Arbocel, washing with ethanol (50 mL). The solvent was removed in vacuo to give the desired compound as a colourless oil, (7.19 g, 98%). ¹H NMR (CD₃OD, 400 MHz) δ 2.60 (s, 1H), 2.91 (t, 1H), 3.08 (q, 1H), 3.31-3.44 (m, 1H), 3.50 (t, 1H), 3.63 (m, 1H), 3.66 (s, 3H), 6.76 (m, 1H), 6.84 (m, 1H), 7.20 (m, 1H); LRMS (EI⁺) 242 [MH⁺].

References:

US2008/234280,2008,A1 Location in patent:Page/Page column 30

3-Pyrrolidinecarboxylic acid, 4-(2,4-difluorophenyl)-1-(1,1-dimethylethyl)-, methyl ester, (3S,4R)-

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References

455957-94-5 Synthesis

(3S,4R)-1-TERT-BUTYL-4-(2,4-DIFLUOROPHENYL)PYRROLIDINE-3-CARBOXYLIC ACID

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References