Hydrochloric Acid → trans-Ethyl-4-phenylpyrrolidine-3-carboxylate hydrochloride

HRID 722394

Reaktionsgleichung

Reaktionsgleichung von HRID 722394
[CH2:1]([O:3][C:4]([C@H:6]1[C@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][N:8](CC2C=CC=CC=2)[CH2:7]1)=[O:5])[CH3:2].[ClH:24]>[Pd].C(O)C>[ClH:24].[CH2:1]([O:3][C:4]([C@H:6]1[C@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 12922288trans-Ethyl 1-benzyl-4-phenylpyrrolidine-3-carboxylate

Produkt 1

HCID 131726062trans-Ethyl-4-phenylpyrrolidine-3-carboxylate hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of trans-ethyl-1-benzyl-4-phenylpyrrolidine-3-carboxylate (1.69 g, 5.47 mmol), concentrated HCl (36% in H2O, 610 mg) and palladium on activated carbon (10 wt %, 169 mg) in ethyl alcohol (27 mL) was put on hydrogenator at 50 psi for overnight. The mixture was filtered through Celite pad and washed with ethyl alcohol. The filtrated was concentrated to give the title compound as a off-white solid (quantitative yield). 1H NMR (400 MHz, CD3OD) δ 1.11 (3H, t, J=6.8 Hz), 3.36–3.42 (2H, m), 3.63–3.75 (4H, m), 4.06–4.11 (2H, m), 7.29–7.39 (5H, m). HPLC purity (retention time): 95% (1.05 min, method C). MS: 220.23 (MH+).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite pad
  2. washwashed with ethyl alcohol
  3. concentrationThe filtrated was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-cf93205eec9a4ce9903197ec4224011e
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138423B2

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