1-Adamantanecarboxylic acid → Tricyclo(3.3.1.13,7)decane-1-carboxamide

HRID 1049292

Reaktionsgleichung

Reaktionsgleichung von HRID 1049292
[C:1]12([C:11]([OH:13])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C1N=C[N:16](C(N2C=NC=C2)=O)C=1.[NH4+].[OH-]>CCOC(C)=O>[C:1]12([C:11]([NH2:16])=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Komponenten

5

Edukt 3

HCID 132351-Adamantanecarboxylic acidHCID 14923Ammonium HydroxideHCID 682631,1'-Carbonyldiimidazole

Produkt 1

HCID 21686Tricyclo(3.3.1.13,7)decane-1-carboxamideAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of adamantane-1-carboxylic acid (2.00 g, 11.10 mmol) in EtOAc (20 mL) was treated with CDI (2.00 g, 12.33 mmol), stirred at RT for 20 minutes, treated with NH4OH (˜14M, 5 mL, ˜70 mmol) and stirred at RT for 20 minutes. The mixture was concentrated to dryness, treated with satd. NaHCO3 and the solids collected via filtration and dried to afford adamantane-1-carboxamide (1.74 g, 87%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.91 (s, 1H), 6.65 (s, 1H), 1.92 (m, 3H), 1.74-1.71 (m, 6H), 1.68-1.57 (m, 6H); MS (ESI) m/z: 180.1 (M+H+).

Aufarbeitung

  1. stirringstirred at RT for 20 minutes
  2. concentrationThe mixture was concentrated to dryness
  3. additiontreated with satd
  4. filtrationNaHCO3 and the solids collected via filtration
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c055df6e0f4f403b8cba3642423ddf68
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382228B2

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