Ammonia → ((3R,4S)-4-Phenylpyrrolidin-3-YL)methanol

HRID 1182166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182166
C([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:10]([CH2:19][OH:20])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+].N>C(O)C.CO.[OH-].[Pd+2].[OH-]>[C:13]1([C@H:11]2[CH2:12][NH:8][CH2:9][C@@H:10]2[CH2:19][OH:20])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

7

Edukt 3

HCID 222AmmoniaHCID 2723923Ammonium formateHCID 21341047((3R,4S)-1-Benzyl-4-phenylpyrrolidin-3-YL)methanol

Produkt 1

HCID 20638814((3R,4S)-4-Phenylpyrrolidin-3-YL)methanolAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To ((3R,4S)-1-benzyl-4-phenyl-pyrrolidin-3-yl)-methanol (2.28 g, 8.54 mmol) in ethanol (200 mL) was added ammonium formate (5.39 g, 85.49 mmol) and palladium hydroxide (446 mg, 20 wt % Pd) and the mixture was refluxed for 1.5h. Ammonia in methanol (0.8 mL, 2M) was added to the reaction mixture and refluxed for an additional 0.5h. The reaction mixture was filtered through celite and concentrated to give ((3R,4S)-4-phenyl-pyrrolidin-3-yl)-methanol as a colorless oil (1.25 g) which was used directly in the next step.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1.5h
  2. temperaturerefluxed for an additional 0.5h
  3. filtrationThe reaction mixture was filtered through celite and
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1989dd61df5045aeaf49f236badc7430
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288548B2

Notizen zur Reaktion

Wird geladen…