(R)-Benzyl 3-((tert-butoxycarbonyl)(methyl)amino)pyrrolidine-1-carboxylate → tert-Butyl methyl((3R)-pyrrolidin-3-yl)carbamate

HRID 1825108

Reaktionsgleichung

Reaktionsgleichung von HRID 1825108
[C:1]([O:5][C:6]([N:8]([CH3:24])[C@@H:9]1[CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[CH3:24][N:8]([C@@H:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 58940619(R)-Benzyl 3-((tert-butoxycarbonyl)(methyl)amino)pyrrolidine-1-carboxylate

Produkt 1

HCID 7019173tert-Butyl methyl((3R)-pyrrolidin-3-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of benzyl (3R)-3-[(tert-butoxycarbonyl)(methyl)amino]pyrrolidine-1-carboxylate 34a (1.5 g, 5.17 mmole) in MeOH (10 ml) was added Pd(OH)2 on carbon (150 mg). The reaction mixture was under 1 atmosphere of H2 overnight, filtered through celite and concentrated, in vacuo. The residue obtained was used directly in the subsequent reaction without any further purification, vide infra. 1H NMR (300 MHz, CD3OD) δ 4.47 (1H, m), 3.20 (1H, m), 2.91 (2H, m), 2.76 (1H, m), 2.69 (3H, s), 1.89 (1H, m), 1.68 (1H, m), 1.35 (9H, s).

Aufarbeitung

  1. customwas under 1 atmosphere of H2 overnight
  2. filtrationfiltered through celite and
  3. concentrationconcentrated, in vacuo
  4. customThe residue obtained
  5. customwas used directly in the subsequent reaction without any further purification, vide infra

Quellen und Nachweise

ORD-Eintrag
ord-312becc83058448da66cc5bd2cd9b9a2
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07045528B2

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