Trifluoroacetic acid → (2R)-5-(3-fluoro-phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid methyl ester

HRID 853781Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:24])[C@H:4]([NH:16]C(OC(C)(C)C)=O)[CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C@H:4]1[CH2:5][CH2:6][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)=[N:16]1)=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2R)-2-tert-butoxycarbonylamino-5-(3-fluoro-phenyl)-5-oxo-pentanoic acid methyl ester (0.57 g, 1.7 mmol) in 1.7 mL of CH2Cl2 at 0° C. was added dropwise 3.8 mL (49 mmol, 29 eq) of TFA. The mixture was stirred at 0° C. for 2 hr. After concentration under vacuum, the residue was dissolved in CH2Cl2 (30 mL), washed with 10% NaHCO3, water, and brine, dried (Na2SO4) and concentrated under vacuum to give (2R)-5-(3-fluoro-phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid methyl ester as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 7.77–7.70 (2H, m), 7.50 (1H, q), 7.27 (1H, tq), 5.05 (1H, tt), 3.90 (3H, s), 3.30–3.00 (2H, m), 2.55–2.30 (2H, m).

Workup

concentrationAfter concentration under vacuum
dissolutionthe residue was dissolved in CH2Cl2 (30 mL)
washwashed with 10% NaHCO3, water, and brine
dry with materialdried (Na2SO4)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-0254a7fa2c9d40e88cc2081924c1aa64
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07256186B2

Reaction notes

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