Benzyl ((3R,4R)-4-hydroxy-1-(2-(4-trifluoromethoxyphenyl)ethanoyl)pyrrolidin-3-yl)carbamate → 1-((3R,4R)-3-amino-4-hydroxypyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone

HRID 1666675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666675
[OH:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:20])[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[CH2:4][C@H:3]1[NH:21]C(=O)OCC1C=CC=CC=1>CO.[Pd]>[NH2:21][C@H:3]1[C@H:2]([OH:1])[CH2:6][N:5]([C:7](=[O:20])[CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]([F:17])([F:18])[F:19])=[CH:13][CH:14]=2)[CH2:4]1

Komponenten

4

Edukt 1

HCID 57970130Benzyl ((3R,4R)-4-hydroxy-1-(2-(4-trifluoromethoxyphenyl)ethanoyl)pyrrolidin-3-yl)carbamate

Produkt 1

HCID 579701111-((3R,4R)-3-amino-4-hydroxypyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanoneAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Benzyl ((3R,4R)-4-hydroxy-1-(2-(4-trifluoromethoxyphenyl)ethanoyl)pyrrolidin-3-yl)carbamate (14 g) was dissolved in methanol (140 mL), followed by addition of 5% Pd—C (2.4 g), and the mixture was stirred overnight under hydrogen atmosphere. The catalyst was removed by filtration, and then the filtrate was concentrated under reduced pressure. The precipitated solids were washed with a mixed solvent of isopropyl ether and hexane to obtain the title compound (8.6 g).

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washThe precipitated solids were washed with a mixed solvent of isopropyl ether and hexane

Quellen und Nachweise

ORD-Eintrag
ord-ca3b781f031747beb8a64589fb37a102
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044068B2

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