Synthesis of Conformationally Constrained 5-Fluoro- and 5-Hydroxymethanopyrrolidines. Ring-Puckered Mimics ofGauche- andAnti-3-Fluoro- and 3-Hydroxypyrrolidines
نویسندگان
چکیده
منابع مشابه
Synthesis of conformationally constrained 5-fluoro- and 5-hydroxymethanopyrrolidines. Ring-puckered mimics of gauche- and anti-3-fluoro- and 3-hydroxypyrrolidines.
N-acetylmethanopyrrolidine methyl ester and its four 5-syn/anti-fluoro and hydroxy derivatives have been synthesized from 2-azabicyclo[2.2.0]hex-5-ene, a 1,2-dihydropyridine photoproduct. These conformationally constrained mimics of idealized C(β)-gauche and C(β)-anti conformers of pyrrolidines were prepared in order to determine the inherent bridge bias and subsequent heteroatom substituent ef...
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In the title compound, C(9)H(6)FNO(2), the carboxyl group is twisted slightly away from the indole-ring plane [dihedral angle = 7.39 (10)°]. In the crystal, carboxyl inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R(2) (2)(8) loops and N-H⋯O hydrogen bonds connect the dimers into (10[Formula: see text]) sheets.
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2011
ISSN: 0022-3263,1520-6904
DOI: 10.1021/jo200117p