2-Bromo-1,1-dimethoxyethane → (1R,2S)-2-(4-chlorophenyl)-1'-(2-(4-(2-(dimethylamino)ethyl)piperazin-1-yl)ethyl) Spiro[cyclopropane-1,3'-indolin]-2'-one

Participants

Reaction Steps

The title compound was prepared in analogy to Example 74 starting from 1-(2-Dimethylamino-ethyl)-piperazine, bromoacetaldehyde dimethyl acetal (commercially available), (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C26H33ClN4O: 452, observed (M+H)+: 453.1 1HNMR (400 MHz, MeOD-d4) δppm 2.15-2.33 (m, 3 H) 2.86 (t, J=5.81 Hz, 3 H) 2.96 (s, 6 H) 3.27 (t, J=8.59 Hz, 3 H) 3.45-3.76 (m, 3 H) 4.32 (d, J=48.76 Hz, 3 H) 6.12 (d, J=7.58 Hz, 1 H) 6.81 (t, J=7.20 Hz, 1 H) 7.11-7.19 (m, 1 H) 7.20-7.28 (m, 3 H) 7.30-7.41 (m, 2 H).

Provenance & Evidence