Isopropyl Acetate → (r)-5-Biphenyl-4-ylmethyl-3-[1-diisopropylamino-meth-(e)-ylidene]-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 588289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588289
F[B-](F)(F)F.C(N(C(C)C)[CH:10]=[N+:11]([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])(C)C.CC(C)([O-])C.[K+].[C:27]([O:31][C:32]([N:34]1[C:38](=[O:39])[CH2:37][CH2:36][C@H:35]1[CH2:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:43][CH:42]=1)=[O:33])([CH3:30])([CH3:29])[CH3:28].C(OC(C)C)(=O)C>C1COCC1>[C:27]([O:31][C:32]([N:34]1[C@H:35]([CH2:40][C:41]2[CH:42]=[CH:43][C:44]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)=[CH:45][CH:46]=2)[CH2:36]/[C:37](=[CH:10]\[N:11]([CH:12]([CH3:13])[CH3:14])[CH:15]([CH3:16])[CH3:17])/[C:38]1=[O:39])=[O:33])([CH3:30])([CH3:28])[CH3:29]

Komponenten

6

Edukt 4

HCID 7915Isopropyl AcetateHCID 11077431N,N,N',N'-tetraisopropylformamidinium tetrafluoroborateHCID 23665647Potassium tert-butoxideHCID 46193436(S)-2-biphenyl-4-ylmethyl-5-oxopyrrolidine-1-carboxylic acid t-butyl ester

Produkt 1

HCID 58160400(r)-5-Biphenyl-4-ylmethyl-3-[1-diisopropylamino-meth-(e)-ylidene]-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

N,N,N′,N′-tetraisopropylformamidinium tetrafluoroborate (2.13 g, prepared according to Example 11) is added to a 1 M solution of potassium-tert-butoxide in THF (5.69 ml). The resulting mixture is then stirred for 1 h at 50° C. (S)-2-Biphenyl-4-ylmethyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (8-a, R1=Boc) (500 mg) is then added and the mixture stirred at 60° C. for 1 h. The mixture is then cooled to room temperature and diluted by addition of 10 ml isopropyl acetate. The mixture is then filtered through silica and concentrated in vacuo to afford (R)-5-biphenyl-4-ylmethyl-3-[1-diisopropylamino-meth-(E)-ylidene]-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (7-a, R1=Boc, R6=iPr, R7=iPr). Spectroscopic data as for Example 19, Method 1.

Aufarbeitung

  1. additionis then added
  2. temperatureThe mixture is then cooled to room temperature
  3. filtrationThe mixture is then filtered through silica
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-90bece41cfb2496c88d42857cdcdfe66
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227934B2

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