(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

HRID 1987510

Reaktionsgleichung

Reaktionsgleichung von HRID 1987510
C1(C)C=CC(C([C@@](C(O)=O)(O)[C@@](C(C2C=CC(C)=CC=2)=O)(O)C(O)=O)=O)=CC=1.[CH3:29][N:30]([CH3:50])[CH2:31][CH2:32][C@H:33]([O:39][C:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][CH:41]=1)[C:34]1[S:35][CH:36]=[CH:37][CH:38]=1.CN(C)CC[C@@H](OC1C2C(=CC=CC=2)C=CC=1)C1SC=CC=1>>[CH3:50][N:30]([CH3:29])[CH2:31][CH2:32][CH:33]([O:39][C:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][CH:41]=1)[C:34]1[S:35][CH:36]=[CH:37][CH:38]=1

Komponenten

4

Edukt 3

HCID 9818212(S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamineHCID 24739908(R)-N,N-dimethyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amineHCID 29414711Di-para-toluoyl-L-tartaric acid

Produkt 1

HCID 11573192N,N-Dimethyl-3-((naphthalen-1-yl)oxy)-3-(thiophen-2-yl)propan-1-amine

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-5e7e9adb22724fcc9f8801b49525ed87
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550605B2

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