Methyl iodide → Exo-8-boc-8-azabicyclo[3.2.1]octane-3-carboxylic acid methyl ester

HRID 711048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711048
[C:1]([O:5][C:6]([N:8]1[C@H:13]2[CH2:14][CH2:15][C@@H:9]1[CH2:10][CH:11]([C:16]([OH:18])=[O:17])[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.C(OCC)(=O)C>[C@@H:13]12[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@@H:9]([CH2:15][CH2:14]1)[CH2:10][CH:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:12]2

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 50999080exo-8-Boc-8-azabicyclo(3.2.1)octane-3-carboxylic acid

Produkt 1

HCID 67491395Exo-8-boc-8-azabicyclo[3.2.1]octane-3-carboxylic acid methyl esterAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (1R,5S)-8-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]octane-3-carboxylic acid (500 mg, 1.96 mmol) in N,N-dimethylformamide (5 mL) was added potassium carbonate (541 mg, 3.92 mmol) and methyl iodide (0.18 mL, 2.94 mmol). The reaction was stirred at room temperature for 18 hours. The reaction was diluted with ethyl acetate (50 mL) and heptanes (50 mL), and then washed with water (100 mL) and brine (50 mL). The organics were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography gave the title compound (486 mg, 92%) as a clear oil. 1H NMR (400 MHz, CDCl3, δ): 4.17-4.29 (m, 2H), 3.65 (s, 3H), 2.75-2.86 (m, 1H), 1.93-2.01 (m, 2H), 1.79-1.92 (m, 2H), 1.67-1.76 (m, 2H), 1.58-1.66 (m, 2H), 1.45 (s, 9H).

Aufarbeitung

  1. washwashed with water (100 mL) and brine (50 mL)
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bcb8417a95954dd780c5d314ab114670
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181252B2

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