trans-Benzyl 3-(tert-butoxycarbonylamino)-4-fluoropyrrolidine-1-carboxylate → tert-Butyl ((3R,4R)-4-fluoropyrrolidin-3-yl)carbamate

HRID 928195

Reaktionsgleichung

Reaktionsgleichung von HRID 928195
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:13]([F:14])[CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[F:14][C@@H:13]1[CH2:12][NH:11][CH2:10][C@H:9]1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4]

Komponenten

4

Edukt 1

HCID 118084929trans-Benzyl 3-(tert-butoxycarbonylamino)-4-fluoropyrrolidine-1-carboxylate

Produkt 1

HCID 58006941tert-Butyl ((3R,4R)-4-fluoropyrrolidin-3-yl)carbamateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (3R,4R)-benzyl 3-((tert-butoxycarbonyl)amino)-4-fluoropyrrolidine-1-carboxylate (3.0 g, 8.8 mmol) in MeOH (50 mL) was added wet Pd/C (0.3 g, 10%) under nitrogen. The suspension was degassed under vacuum and purged with hydrogen three times. The resulting mixture was stirred at rt under hydrogen balloon for 3 hr. The reaction mixture was filtered and the filtrate was concentrated to afford the title compound (1.6 g, 88% yield) as light yellow oil that solidified on standing.

Aufarbeitung

  1. customThe suspension was degassed under vacuum
  2. custompurged with hydrogen three times
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-9c708ef449754d64962de28bb1b2c5b6
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290496B2

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