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Acetic Anhydride → Methyl(2S,4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylate

HRID 1666015
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1666015
[C:1]([N:8]1[CH2:12][C@@H:11]([NH:13][CH:14]2[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:22]([O:24][CH3:25])=[O:23])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:26][C:27](OC(C)=O)=[O:28]>N1C=CC=CC=1>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([C:27](=[O:28])[CH3:26])[CH:14]2[CH2:19][CH2:18][C:17]([CH3:20])([CH3:21])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:22]([O:24][CH3:25])=[O:23])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]
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Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 66970872Methyl(2S,4S)-1-BOC-4-[(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylate

Produkt 1

HCID 67359765Methyl(2S,4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Methyl(2S,4S)-1-BOC-4-[(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylate (1.01 g, 2.84 mmol) obtained in Step A, was dissolved in pyridine (5 mL), and Ac2O (1.34 mL, 14.20 mmol) was added thereto at room temperature. The reaction solution was heated to 90° C. and was stirred for 2 hours. After the reaction was completed, CuSO4.5H2O aqueous solution was added and the solution was extracted with EtOAc. The extracted organic solution was dried over MgSO4 and concentrated in vacuo. The obtained residue was purified by column chromatography (eluent: EtOAc/Hex=1/1) to give the title compound (0.98 g, 87%).

Aufarbeitung

  1. customat room temperature
  2. extractionthe solution was extracted with EtOAc
  3. dry with materialThe extracted organic solution was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by column chromatography (eluent: EtOAc/Hex=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-573b6e85a71b4ff999678f5f2487ff05
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08039622B2

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