Triethylamine → (1RS,2SR,6RS,7SR)-4-(3,5-dimethylbiphenyl-4-yl)-5-oxo-10-oxa-tricyclo[5.2.1.02,6]dec-3-en-3-yl 2,2-dimethylpropionate

HRID 1430767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1430767
[CH3:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:5]=[C:6]([CH3:20])[C:7]=1[CH:8]1[C:16](=[O:17])[CH:15]2[CH:10]([CH:11]3[O:18][CH:14]2[CH2:13][CH2:12]3)[C:9]1=[O:19].C(N(CC)CC)C.[C:34](Cl)(=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36]>ClCCl>[CH3:36][C:35]([CH3:38])([CH3:37])[C:34]([O:19][C:9]1[CH:10]2[CH:15]([C:16](=[O:17])[C:8]=1[C:7]1[C:2]([CH3:1])=[CH:3][C:4]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:5][C:6]=1[CH3:20])[CH:14]1[O:18][CH:11]2[CH2:12][CH2:13]1)=[O:39]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 67777251(1RS,2SR,6RS,7SR)-4-(3,5-dimethylbiphen-4-yl)-10-oxa-tricyclo[5.2.1.02,6]decane-3,5-dione

Produkt 1

HCID 67777293(1RS,2SR,6RS,7SR)-4-(3,5-dimethylbiphenyl-4-yl)-5-oxo-10-oxa-tricyclo[5.2.1.02,6]dec-3-en-3-yl 2,2-dimethylpropionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (1RS,2SR,6RS,7SR)-4-(3,5-dimethylbiphenyl-4-yl)-10-oxa-tricyclo-[5.2.1.02,6]decane-3,5-dione (80 mg, 0.23 mmol) in dichloromethane (5 ml) and triethylamine (140 μl, 1 mmol) is added pivaloyl chloride (124 μl, 1 mmol) at room temperature. The reaction mixture is stirred overnight at room temperature. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR)-4-(3,5-dimethylbiphenyl-4-yl)-5-oxo-10-oxa-tricyclo[5.2.1.02,6]dec-3-en-3-yl 2,2-dimethylpropionate.

Aufarbeitung

  1. additionSilica gel is added to the crude
  2. customreaction mixture
  3. customthe solvent is evaporated under reduced pressure
  4. customthe residue is purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-41fd8b736d794217b5729eab761df3c9
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940913B2

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