Benzene, 1-iodo-4-(trifluoromethyl)- → (9S)-9-(tert-butyldimethylsilyloxy)-4-chloro-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3-ol

HRID 573789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573789
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.C([Li])(C)(C)C.[Si:17]([O:24][C@H:25]1[CH2:34][C:33]([CH3:36])([CH3:35])[CH2:32][C:31]2[N:30]=[C:29]([Cl:37])[C:28]3[C:38](=[O:46])[O:39][C:40]4([CH2:45][CH2:44][O:43][CH2:42][CH2:41]4)[C:27]=3[C:26]1=2)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>O1CCCC1.CCCCC>[Si:17]([O:24][C@H:25]1[CH2:34][C:33]([CH3:36])([CH3:35])[CH2:32][C:31]2[N:30]=[C:29]([Cl:37])[C:28]3[C:38]([C:2]4[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=4)([OH:46])[O:39][C:40]4([CH2:41][CH2:42][O:43][CH2:44][CH2:45]4)[C:27]=3[C:26]1=2)([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18]

Komponenten

6

Edukt 3

HCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 86662531(S)-9-(tert-butyldimethylsilyloxy)-4-chloro-7,7-dimethyl-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3-oneHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 86662530(9S)-9-(tert-butyldimethylsilyloxy)-4-chloro-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-65 °C

Versuchsvorschrift

2.31 g 1-Iodo-4-(trifluoromethyl)benzene are dissolved in 30 ml tetrahydrofurane, cooled to −65° C. and treated dropwise with 9.2 ml of a 1.6 M solution of tert.-butyllithium in n-pentan. The mixture is stirred for 30 minutes and then a solution of 1.9 g (S)-9-(tert-butyldimethylsilyloxy)-4-chloro-7,7-dimethyl-2′,3′,5′,6,6′,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4′-pyran]-3-one in 30 ml tetrahydrofurane is added dropwise. The mixture is stirred for 30 minutes at −65° C. and for 30 minutes at −50° C. Then the reaction is quenched by addition of 0.5 ml methanol. The mixture is partitioned between 0.1 M hydrochloric acid and ethylacetate. The aqueous phase is twice extracted with ethylacetate. The combined organic phases are dried with sodium sulphate and the solvents are evaporated in vacuo. The residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 80:20).

Aufarbeitung

  1. stirringThe mixture is stirred for 30 minutes at −65° C. and for 30 minutes at −50° C
  2. customThen the reaction is quenched by addition of 0.5 ml methanol
  3. customThe mixture is partitioned between 0.1 M hydrochloric acid and ethylacetate
  4. extractionThe aqueous phase is twice extracted with ethylacetate
  5. dry with materialThe combined organic phases are dried with sodium sulphate
  6. customthe solvents are evaporated in vacuo
  7. customThe residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 80:20)

Quellen und Nachweise

ORD-Eintrag
ord-e785afbd5aa6450a9adf06ae8e5a5238
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029544B2

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