Methyl (4S)-4-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopent-2-ene-1-carboxylate → methyl (3S)-3-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopentanecarboxylate

HRID 270593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 270593
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C:12]([C:18]([OH:21])([CH3:20])[CH3:19])([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][CH2:11][C:12]([C:18]([OH:21])([CH3:20])[CH3:19])([C:14]([O:16][CH3:17])=[O:15])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

3

Edukt 1

HCID 86602445Methyl (4S)-4-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopent-2-ene-1-carboxylate

Produkt 1

HCID 86602446methyl (3S)-3-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopentanecarboxylateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Methyl (4S)-4-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopent-2-ene-1-carboxylate (1.4 g, 4.7 mmol) was dissolved in ethanol (30 mL) in a Parr flask and purged with N2. 10% Palladium on carbon (0.14 g) was added and the mixture was shaken overnight under nitrogen at 50 psi. The mixture was filtered through celite, washed with methylene chloride and concentrated to give the desired product (1.06 g, 86%).

Aufarbeitung

  1. custompurged with N2
  2. addition10% Palladium on carbon (0.14 g) was added
  3. filtrationThe mixture was filtered through celite
  4. washwashed with methylene chloride
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-286732c1b18c4772abc87f0dd730cbac
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449467B2

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