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

HRID 588288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588288
CC(C)([O-])C.[K+].F[P-](F)(F)(F)(F)F.[CH:14]([N+:17]([CH:25]([CH3:27])[CH3:26])=[CH:18]N1CCCCC1)([CH3:16])[CH3:15].[C:28]([O:32][C:33]([N:35]1[C:39](=[O:40])[CH2:38][CH2:37][C@H:36]1[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:44][CH:43]=1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>C1COCC1.C(OC(C)C)(=O)C>[C:28]([O:32][C:33]([N:35]1[C@H:36]([CH2:41][C:42]2[CH:43]=[CH:44][C:45]([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)=[CH:46][CH:47]=2)[CH2:37]/[C:38](=[CH:18]\[N:17]([CH:14]([CH3:15])[CH3:16])[CH:25]([CH3:26])[CH3:27])/[C:39]1=[O:40])=[O:34])([CH3:31])([CH3:29])[CH3:30]

Komponenten

6

Edukt 3

HCID 23665647Potassium tert-butoxideHCID 46193436(S)-2-biphenyl-4-ylmethyl-5-oxopyrrolidine-1-carboxylic acid t-butyl esterHCID 178457509HCID 178457509, Verbindung

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 2

HCID 7915Isopropyl AcetateLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 1 M solution of potassium tert-butoxide in THF (11.7 ml) is added to diisopropyl(piperidin-1-ylmethylidene)ammonium hexafluorophosphate (5 g, prepared according to Example 12). 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) (1 g) is then added to the reaction and the resulting mixture is stirred for 1 h at room temperature. The mixture is diluted with isopropyl acetate and filtered through silica. The residue is concentrated in vacuo then purified by column chromatography (ethyl acetate) to give (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). Rf 0.55 (ethyl acetate). 1H NMR (DMSO-d6), 7.65-7.62 (2H), 7.61-7.58 (2H), 7.47-7.42 (2H), 7.37-7.31 (1H), 7.29-7.25 (2H), 7.01 (1H), 4.28-4.20 (1H), 3.84-3.70 (2H), 3.07-3.01 (1H), 2.82-2.73 (1H), 2.71-2.63 (1H) 2.49-2.44 (1H), 1.49 (9H), 1.13-1.08 (12H).

Aufarbeitung

  1. additionis then added to the reaction
  2. filtrationfiltered through silica
  3. concentrationThe residue is concentrated in vacuo
  4. customthen purified by column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8b24c4f453ae4c97a74bb0db42b08e32
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227934B2

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