Hydrochloric Acid → (S)-2-(4-p-Tolyloxy-phenoxymethyl)-pyrrolidine (S)-2-(4-p-tolyloxyphenoxymethyl)-pyrrolidine HCl

HRID 1909654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1909654
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:29]>O1CCOCC1>[ClH:29].[C:25]1([CH3:28])[CH:24]=[CH:23][C:22]([O:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@@H:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[CH:16][CH:17]=2)=[CH:27][CH:26]=1.[C:25]1([CH3:28])[CH:24]=[CH:23][C:22]([O:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@@H:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[CH:16][CH:17]=2)=[CH:27][CH:26]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 68999151(S)-2-(4-p-Tolyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 69401061(S)-2-(4-p-Tolyloxy-phenoxymethyl)-pyrrolidine (S)-2-(4-p-tolyloxyphenoxymethyl)-pyrrolidine HClAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(S)-2-(4-p-Tolyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.02 g, 7.88 mmol) was taken into 4M HCl in dioxane (10 mL) and reacted at room temperature for 12 h. The mixture was concentrated to dryness to obtain the title product (2.35 g, 7.35 mmol, 93% yield); MS; m/z 320, found 284 (M-36HCl); 1H NMR (400 MHz, DMSO-d6) δ 1.70-1.78 (m, 1H), 1.87-1.94 (m, 1H), 1.96-2.01 (m, 1H), 2.08-2.14 (m, 1H), 2.27 (s, 3H), 3.17-3.24 (m, 2H), 3.86-3.92 (m, 1H), 4.10-4.15 (m, 1H), 4.20-4.24 (m, 1H), 6.82-6.84 (d, J=8.0, 2H), 6.99-7.0 (m, 4H), 7.15-7.17 (d, J=8.0, 2H), 9.34 (s, 1H).

Aufarbeitung

  1. customreacted at room temperature for 12 h
  2. concentrationThe mixture was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-64499765105140a9b05b8fcdf581cee8
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598359B2

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