4-(3-Fluoro-phenoxymethyl)-pyrroline-1,2-dicarboxylic acid di-tert-butyl ester → (2S,4S)-4-(3-fluoro-phenoxymethyl)-pyrrolidine-2-carboxylic acid

HRID 2113919Notes

Reaction equation

C(OC([N:8]1[CH2:12][CH:11]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH:10]=[C:9]1[C:22]([O:24]C(C)(C)C)=[O:23])=O)(C)(C)C>Cl.O1CCOCC1>[F:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[O:14][CH2:13][C@@H:11]1[CH2:12][NH:8][C@H:9]([C:22]([OH:24])=[O:23])[CH2:10]1

Participants

Conditions

Temperature: 50 °C

Procedure

4-(3-fluoro-phenoxymethyl)-pyrroline-1,2-dicarboxylic acid di-tert-butyl ester (Preparation 5, 475 mg, 1.2 mmol) was dissolved in a solution of anhydrous hydrogen chloride in dioxane (4M, 15 ml) and stirred at 50° C. under a nitrogen atmosphere for 1 hour. The solvent was removed under reduced pressure and the resulting semi-solid triturated with ethyl acetate to give a white solid which was recrystallised from ethyl acetate/isopropyl alcohol to give the title compound as a mixture of diastereomers (˜5:1 2S,4S:2S,4R) as a white solid hydrochloride salt (90 mg, 35%)

Workup

customThe solvent was removed under reduced pressure
customthe resulting semi-solid triturated with ethyl acetate
customto give a white solid which
customwas recrystallised from ethyl acetate/isopropyl alcohol

Sources & evidence

ORD record: ord-2fc530a0aa1f4592b522c7a923c1165c
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432299B2

Reaction notes

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