Hydrochloric Acid → (R)-2-(4-Prop-2-ynyloxy-phenoxymethyl)-pyrrolidine hydrochloride

HRID 12925

Reaktionsgleichung

Reaktionsgleichung von HRID 12925
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]#[CH:24])=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:25]>O1CCOCC1>[ClH:25].[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:16][CH:17]=1)[C:23]#[CH:24]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 866196562-(4-Prop-2-ynyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 24897721(R)-2-(4-Prop-2-ynyloxy-phenoxymethyl)-pyrrolidine hydrochlorideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of the product from step 3 (100 mg) was added 2M HCl in dioxane (4 mL) and the resulting mixture was stirred for 2 h, and the solvent was removed in vacuo. Crude material was triturated with ether to obtain the title product (70 mg, 100%); LCMS; 97%, m/z 232.1 (M+1); 1H NMR (DMSO-d6, 400 MHz) δ 1.70 (1H, m), 1.95 (2H, m), 2.10 (2H, m), 3.20 (2H, m), 3.53 (2H, m), 3.86 (1H, m), 4.07 (1H, dd, J1=8.0 Hz, J2=10.0 Hz), 4.18 (1H, dd, J1=4.0 Hz, J2=10.8 Hz), 6.94 (4H, s), 9.2 (2H, br s).

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customCrude material was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-9713988b229b47619733e20c7dc5b7fa
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728032B2

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