Pyrrolidine → HCID 57571228, Verbindung

HRID 1971290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1971290
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC[N:22]([CH:26]([CH3:28])C)[CH:23]([CH3:25])C.ClC(OCC(C)C)=O.N1CCCC1>C(Cl)Cl>[O:19]=[C:17]([N:22]1[CH2:23][CH2:25][CH2:28][CH2:26]1)[C@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH2:10][C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 31268PyrrolidineHCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 7020844(2S)-2-(((tert-butoxy)carbonyl)amino)-3-(pyridin-4-yl)propanoic acid

Produkt 1

HCID 57571228HCID 57571228, VerbindungAusbeute 24,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-Boc-(5)-3-(pyridin-4-yl)alanine (0.500 g, 1.88 mmol) was dissolved in CH2Cl2 (15 mL) and DIEA (361 μL, 2.07 mmol) was added. The mixture was cooled to 0° C. and isobutyl chloroformate (270 μL, 2.07 mmol) was added. The mixture was stirred for 10 min and pyrrolidine (267 mg, 3.76 mmol) in CH2Cl2 (5 mL) was added. This mixture was stirred for 15 min at 4° C., 12 h at 25° C., washed successively with NaH2PO4, saturated sodium hydrogen carbonate, water and brine. The organic layer was dried over magnesium sulfate and evaporated to dryness. The residue obtained was purify by column chromatography (SiO2) using a gradient of MeOH 0-10% [v/v] in EtOAc to give tert-butyl (R)-1-oxo-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-2-ylcarbamate EBE 06172 (146 mg, 24% yield) as a white solid.

Aufarbeitung

  1. stirringThis mixture was stirred for 15 min at 4° C., 12 h at 25° C.
  2. washwashed successively with NaH2PO4, saturated sodium hydrogen carbonate, water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue obtained
  6. customwas purify by column chromatography (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-b94b72412c264abf84c86572793fdbde
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431599B2

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