4-(Chloromethyl)piperidine → (1R,2S)-2-(4-chlorophenyl)-1'-(piperidin-4-ylmethyl) Spiro[cyclopropane-1,3'-indolin]-2'-one

Participants

Reaction Steps

The title compound was prepared in analogy to Example 70 starting from 4-(chloromethyl)piperidine (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 C22H23ClN2O: 366, observed (M+H)+: 367.2 1HNMR (400 MHz, MeOD-d4) δppm 1.51-1.67 (m, 2 H) 1.96 (br. s., 2 H) 2.12-2.21 (m, 2 H) 2.21-2.35 (m, 1 H) 2.93-3.07 (m, 2 H) 3.22 (t, J=8.59 Hz, 1 H) 3.38-3.50 (m, 2 H) 3.84 (d, J=7.33 Hz, 2 H) 6.09 (d, J=7.58 Hz, 1 H) 6.77 (t, J=7.58 Hz, 1 H) 7.11 (d, J=7.83 Hz, 1 H) 7.16-7.26 (m, 3 H) 7.29-7.35 (m, 2 H).

Provenance & Evidence