2-Chloro-3-ethyl-4-fluorobenzonitrile → rel-2-Chloro-4-[[(1R,2S,3R)-2,3-dihydroxy-2-methyl-cyclopentyl]amino]-3-ethyl-benzonitrile

Participants

Reaction Steps

The title compound is prepared by essentially following the procedure described in Example 20, using rel-(1S,2R,5R)-2-amino-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol and 2-chloro-3-ethyl-4-fluoro-benzonitrile for the substitution reaction followed by TBDPS removal with TBAF. 1H-NMR (400 MHz, DMSO-d6) δ 7.44 (d, J=8.7 Hz, 1H), 6.87 (d, J=9.0 Hz, 1H), 5.74-5.70 (m, 1H), 4.74 (d, J=5.4 Hz, 1H), 4.27 (s, 1H), 3.82-3.79 (m, 1H), 3.58-3.51 (m, 1H), 2.80-2.78 (m, 2H), 2.03-2.02 (m, 1H), 1.88-1.86 (m, 1H), 1.69-1.68 (m, 1H), 1.52-1.51 (m, 1H), 1.01-0.97 (m, 3H), 0.93 (s, 3H). LC-ES/MS m/z 295 (M+1).

Provenance & Evidence