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Methyl iodide → HCID 86646601, Verbindung

HRID 1963238
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1963238
[NH:1]1[C:5]([CH:6]2[CH2:11][CH:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9][CH2:8][N:7]2[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[N:4][N:3]=[N:2]1.IC.[C:29]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:29][N:3]1[N:2]=[N:1][C:5]([CH:6]2[CH2:11][CH:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9][CH2:8][N:7]2[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])=[N:4]1.[CH3:29][N:4]1[C:5]([CH:6]2[CH2:11][CH:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9][CH2:8][N:7]2[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])=[N:1][N:2]=[N:3]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469255HCID 178469255, Verbindung

Produkt 2

HCID 66734713HCID 66734713, VerbindungAusbeute 32 %HCID 86646601HCID 86646601, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180
Acetone
Lösungsmittel

Versuchsvorschrift

1-Benzyl 4-ethyl 2-(1H-tetrazol-5-yl)piperidine-1,4-dicarboxylate (3.45 g, 9.60 mmol) was dissolved in acetone (20 mL) and iodomethane (2.99 mL, 48.00 mmol) and K2CO3 (3.98 g, 28.80 mmol) were added. The mixture was stirred at room temperature for 3 h. The reaction mixture was partitioned between water and EtOAc. The aqueous layer was extracted twice with EtOAc and the combined organic phase was washed with water and evaporated. The crude product was purified on a 100 g Biotage column with heptane/EtOAc 88/12-0/100 over 12 column volumes (CV). 1-Benzyl 4-ethyl 2-(2-methyl-2H-tetrazol-5-yl)piperidine-1,4-dicarboxylate (1.84 g, 51%) and 1-benzyl 4-ethyl 2-(1-methyl-1H-tetrazol-5-yl)piperidine-1,4-dicarboxylate (1.14 g, 32%) were isolated. 2-Methyl-isomer: 1H NMR (400 MHz, cdcl3) δ 1.15 (t, 3H), 1.75-1.87 (m, 1H), 2.02-2.11 (m, 1H), 2.27-2.37 (m, 1H), 2.66-2.78 (m, 2H), 3.55-3.65 (m, 1H), 3.75-3.86 (m, 1H), 3.90-3.99 (m, 1H), 4.01-4.09 (m, 1H), 4.25 (s, 3H), 5.13 (q, 2H), 5.55-5.62 (m, 1H), 7.25-7.38 (m, 5H). MS m/z 374 (M+H)+. 3-Methyl-isomer: MS m/z 374 (M+H)+

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. washthe combined organic phase was washed with water
  4. customevaporated
  5. customThe crude product was purified on a 100 g Biotage column with heptane/EtOAc 88/12-0/100 over 12 column volumes (CV)

Quellen und Nachweise

ORD-Eintrag
ord-693130be051b4bf4bbf326f17a010ea6
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08415378B2

Notizen zur Reaktion

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