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

HRID 657714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657714
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 refluxed for 1.5 h. Ammonia in methanol (0.8 mL, 2M) was added to the reaction mixture and refluxed for an additional 0.5 h. 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. temperaturerefluxed for 1.5 h
  2. temperaturerefluxed for an additional 0.5 h
  3. filtrationThe reaction mixture was filtered through celite and
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f305e9aadcc94217b2b0aa3e02b80b34
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076349B2

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