(S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine → N,N-Dimethyl-3-((naphthalen-1-yl)oxy)-3-(thiophen-2-yl)propan-1-amine

Participants

Reaction Steps

Di-para-toluoyl-L-tartaric acid works as an efficient resolving agent for preparation of (S)-isomer of compound of formula 4, for example, (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine. The R-isomer enriched mother liquor containing (R)-(−)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine can be racemized to obtain (±)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine by treatment with a base, which can be further recycled and subjected to resolution process with DPTTA, thereby increasing the yield of desired enantiomer, (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine.

Provenance & Evidence