Tetrahedron letters

Synthesis of 1, 2-disubstituted pyrroles: A cis peptide bond surrogate

AD Abell, DA Hoult, EJ Jamieson

Index: Abell, Andrew D.; Hoult, Deborah A.; Jamieson, Emily J. Tetrahedron Letters, 1992 , vol. 33, # 39 p. 5831 - 5832

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Citation Number: 29

Abstract

Preparation of 12. NaCNBH 3 (0.8 equiv) was added to 9 (310mg) and ammonium acetate (8 equiv) in MeOH (7 mL). 12 was isolated by vacuum filtration as a hydroscopic solid after 18h stirring at RT. Data for 12: mp 167–171°. 1 H NMR (300MHz, D 2 O) δ 4.13 (2H, s); 4.49 (2H, s); 6.13 (1H, m); 6.33 (1H, m); 6.76 (1H, m). 13 C NMR (D 2 O) δ 41.4, 51.6, 108.6, 113.3, 123.0, 126.7, 177.5. IR(KBr) 3191, 2361, 1576 cm −1 . Found C, 49.12; H, 6.98; N, 16.46. ...