Ammonium Chloride → (1RS)-1-phenyl-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl)pyrrolidin-2-yl]methanol

HRID 248894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 248894
[CH2:1]([N:8]([CH3:22])[C:9]([CH2:11][CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]=[O:21])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>C1COCC1>[C:23]1([CH:20]([C@@H:16]2[CH2:17][CH2:18][CH2:19][N:15]2[C:13](=[O:14])[CH2:12][CH2:11][C:9](=[O:10])[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:22])[OH:21])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 14674666(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-alHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 15661001(1RS)-1-phenyl-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl)pyrrolidin-2-yl]methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of (2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-al (200 mg) in THF (5 ml) was cooled to -25° C. A solution of phenyl magnesium bromide in THF (2M, 0.49 ml) was added dropwise to the solution. The reaction solution was stirred for 30 mins, at the same temperature, and for 30 mins at 0° C. A saturated aq. solution of ammonium chloride was added to the reaction solution. The mixture was extracted with EtOAc. The extract was washed, dried, and evaporated. The residue was purified by column chromatography on silica gel (EtOAc-CH3OH) to give the title compound (45 mg) having the following physical data:

Aufarbeitung

  1. waitfor 30 mins at 0° C
  2. extractionThe mixture was extracted with EtOAc
  3. washThe extract was washed
  4. customdried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (EtOAc-CH3OH)

Quellen und Nachweise

ORD-Eintrag
ord-df7d6e916cf24b8e8094d3311e81cbd3
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212191

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