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

HRID 20202

반응식

HRID 20202 반응식
[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]

참가 물질

10

반응물 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

생성물 1

HCID 576937077-(1H-Indole-3-carbonyloxy)-9-methoxycarbonylmethyl-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester수율 89.5%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-035ea214a9664fb0b0a198a21ab33606
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745628B2

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