Piperazine → (1R,2S)-2-(4-chlorophenyl)-1'-(3-(piperazine-1-carbonyl)benzyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Participants

Reaction Steps

The title compound was prepared in analogy to Example 60 starting from piperazine, (3-bromomethyl)-benzoate (commercially available), (1R,2S) and (1S,2R)-3-((2-(4-chlorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)methyl)benzoic acid prepared as in Scheme 1. LC/MS m/e calcd. for C28H26ClN3O2: 471, observed (M+H)+: 472.2 1H NMR (400 MHz, MeOD-d4) δppm 2.17-2.30 (m, 2 H) 3.51 (br. s., 8 H) 3.21-3.35 (m, 1 H) 5.04-5.23 (m, 2 H) 6.10 (d, J=7.58 Hz, 1 H) 6.74 (t, J=7.45 Hz, 1 H) 6.95 (d, J=7.83 Hz, 1 H) 7.05-7.16 (m, 1 H) 7.23 (d, J=8.34 Hz, 2 H) 7.29-7.38 (m, 2 H) 7.40-7.49 (m, 2 H) 7.49-7.58 (m, 2 H).

Provenance & Evidence