(S)-benzyl 4-(3-(tert-butoxycarbonylamino)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate → (S)-benzyl 4-(3-amino-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

HRID 407876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407876
C(OC([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:16][CH2:15]2)[C:10]1=[O:30])=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:16][CH2:15]2)[C:10]1=[O:30]

Komponenten

3

Edukt 1

HCID 86688075(S)-benzyl 4-(3-(tert-butoxycarbonylamino)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

Produkt 1

HCID 86688074(S)-benzyl 4-(3-amino-2-oxopyrrolidin-1-yl)piperidine-1-carboxylateAusbeute 64,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

A solution of (S)-benzyl 4-(3-(tert-butoxycarbonylamino)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (7 g, 17 mmol) in 50% TFA/CH2Cl2 (50 mL) was stirred at ambient temperature for 1 hour. The mixture was concentrated in vacuo. The residue was dissolved in EtOAc (200 mL) and washed with saturated sodium carbonate (200 mL) and brine. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to yield (S)-benzyl 4-(3-amino-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (3.4 g, 11 mmol, 64%).

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (200 mL)
  3. washwashed with saturated sodium carbonate (200 mL) and brine
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-67866b5ebd984072812ab2bf1165ca33
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754226B2

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