Trifluoroacetic anhydride → 7-(1H-Indole-3-carbonyloxy)-9-methoxycarbonylmethyl-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

HRID 20202

Reaktionsgleichung

Reaktionsgleichung von HRID 20202
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:26][O:27][C:28]([CH:30]1[CH2:37][CH:36]2[N:38]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH:32]([CH2:33][CH:34](O)[CH2:35]2)[CH2:31]1)=[O:29].ClCCl.CO.N.[Mn]([O-])(=O)(=O)=O.[K+].C(=O)(O)[O-].[Na+]>ClCCl.CN(C1C=CN=CC=1)C.O>[CH3:26][O:27][C:28]([CH:30]1[CH2:37][CH:36]2[N:38]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH:32]([CH2:33][CH:34]([O:11][C:10]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)=[O:12])[CH2:35]2)[CH2:31]1)=[O:29]

Komponenten

10

Edukt 6

HCID 9845Trifluoroacetic anhydrideHCID 69867Indole-3-Carboxylic AcidHCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 21584172Ammonia methanol dichloromethaneHCID 578944079-Azabicyclo[3.3.1]nonane-9-aceticacid, 3-(methoxycarbonyl)-7-oxo-, methyl ester

Produkt 1

HCID 576937077-(1H-Indole-3-carbonyloxy)-9-methoxycarbonylmethyl-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl esterAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Indole-3-carboxylic acid (6.43 gr, 39.9 mmol) is added in portions to a solution of 5.33 mL (37.7 mmol) of trifluoroacetic anhydride in dichloromethane (172 mL) and under nitrogen atmosphere. The resulting suspension is left under stirring for 30 minutes. 7-hydroxy-9-methoxycarbonylmethyl-9-aza-bicyclo[3.3.1]nonan-3-carboxylic acid methyl ester (6 gr, 22.1 mmol) dissolved in dichloromethane (15 mL) is then added dropwise. Next, a catalytic amount of DMAP is added, and the suspension is then left under stirring for 4 h. Following that time, and once the limiting starting product has been used up as shown by thin-layer chromatography (dichloromethane/methanol/ammonia 90:10:1, which reveals potassium permanganate), water (50 mL) is added to the reaction mixture and the mixture is basified with a saturated aqueous solution of sodium bicarbonate. Following filtration to remove the remains of indole-3-carboxylic acid in excess, the resulting phases are separated. The organic phase is dried over magnesium sulphate and evaporated to dryness, to give 7-(1H-Indole-3-carbonyloxy)-9-methoxycarbonylmethyl-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester as a white solid (8.20 gr, 89%) that can be used directly in the following synthesis step.

Aufarbeitung

  1. waitThe resulting suspension is left
  2. additionis then added dropwise
  3. waitthe suspension is then left
  4. stirringunder stirring for 4 h
  5. additionis added to the reaction mixture
  6. filtrationfiltration
  7. customto remove the remains of indole-3-carboxylic acid in excess, the resulting phases
  8. customare separated
  9. dry with materialThe organic phase is dried over magnesium sulphate
  10. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-035ea214a9664fb0b0a198a21ab33606
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745628B2

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