Thioanisole → Methyl (3s,7as)-6-benzyloxycarbonylamino-5-oxohexahydropyrrolizine-3-carboxylate

HRID 10424

Reaktionsgleichung

Reaktionsgleichung von HRID 10424
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:30]([O:32]C)=O)[CH2:13][C@H:14]1[N:18](C(OC(C)(C)C)=O)[C@H:17]([C:26]([O:28][CH3:29])=[O:27])[CH2:16][CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:13][C@H:14]2[N:18]([C@H:17]([C:26]([O:28][CH3:29])=[O:27])[CH2:16][CH2:15]2)[C:30]1=[O:32])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 7520ThioanisoleHCID 1317258971-Tert-butyl 2-methyl (2s,5s)-5-(2-benzyloxycarbonylamino-2-methoxycarbonylethyl)pyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 91509044Methyl (3s,7as)-6-benzyloxycarbonylamino-5-oxohexahydropyrrolizine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

1500 mg of 1-tert-butyl 2-methyl (2S,5S)-5-(2-benzyloxycarbonylamino-2-methoxycarbonylethyl)pyrrolidine-1,2-dicarboxylate were mixed with 0.2 ml of thioanisole. Then 10 ml of trifluoroacetic acid were added, and the mixture was stirred for 45 min. The solvents were then removed in vacuo, and the residue was taken up in 10 ml of pyridine. 1.1 ml of diisopropylethylamine were added, and the mixture was heated at 95° C. for 3 h. The solvents were removed in vacuo, and the residue was chromatographed on silica gel.

Aufarbeitung

  1. customThe solvents were then removed in vacuo
  2. addition1.1 ml of diisopropylethylamine were added
  3. customThe solvents were removed in vacuo
  4. customthe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-cb72a94ce0d34f9d96a25ac130802067
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094800B2

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