1,2-Dichloroethane → HCID 66970642, Verbindung

Beteiligte Stoffe

Reaktionsschritte

4-(5-Chloro-2-methoxyphenyl)-4-methoxypiperidine 5d (51 mg, 0.2 mmol) was dissolved in 1,2-dichloroethane (1.5 mL) and treated with (S,S,S)-norbornene carboxaldehyde (24 mg, 0.2 mmol, 1.0 eq), followed by the addition of NaBH(OAc)3 (65 mg, 0.3 mmol, 1.5 eq). The reaction was allowed to stir at room temperature for 1 h, quenched with methanol (1 mL) and allowed to stir for another 30 min (until gas evolution stopped). The crude reaction mixture was purified by HPLC (10-99 CH3CN gradient, 0.05% TFA) to provide the desired product 1-(((1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl)methyl)-4-(5-chloro-2-methoxyphenyl)-4-methoxypiperidine (compound no. 140) as the TFA salt. LC/MS (RP-C18, 10-99% CH3CN/0.05% TFA gradient over 5 min) m/z 362.2 [M+H]+, retention time 2.53 min.

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