N-Methylmorpholine N-oxide monohydrate → 2-Hydroxy-6-methoxy-3,3-dimethyl-2,3-dihydro-1H-benzo[b]pyrano[3,2-h]-acridine-1,7(14H)-dione

HRID 478695

Reaktionsgleichung

Reaktionsgleichung von HRID 478695
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[O:25][C:24]([CH3:27])([CH3:26])[CH:23]=[CH:22][C:6]2=[C:7]2[C:16]=1[C:15](=[O:17])[C:14]1[CH:13]=[C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]3=[CH:10][C:9]=1[NH:8]2.[OH2:28].C[N+]1([O-])CC[O:33]CC1.OS([O-])=O.[Na+]>C(O)(C)(C)C.O1CCCC1.O.CC(O)(C)C.[Os](=O)(=O)(=O)=O>[OH:28][CH:23]1[C:24]([CH3:27])([CH3:26])[O:25][C:5]2[C:6](=[C:7]3[C:16](=[C:3]([O:2][CH3:1])[CH:4]=2)[C:15](=[O:17])[C:14]2[CH:13]=[C:12]4[CH:18]=[CH:19][CH:20]=[CH:21][C:11]4=[CH:10][C:9]=2[NH:8]3)[C:22]1=[O:33]

Komponenten

7

Edukt 3

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 220645146-Methoxy-3,3-dimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-oneHCID 23665763Sodium Bisulfite

Produkt 1

HCID 220645082-Hydroxy-6-methoxy-3,3-dimethyl-2,3-dihydro-1H-benzo[b]pyrano[3,2-h]-acridine-1,7(14H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 6386tert-ButanolLösungsmittelHCID 22124471t-Butanol tetrahydrofuran waterLösungsmittel2×

Versuchsvorschrift

To a solution of 1.33 mmol of the compound obtained in Step 2 in 30 ml of a 10/3/1 mixture of tert-butanol/tetrahydrofuran/water there are added osmium tetroxide in the form of a 2.5% solution in 0.67 ml of 2-methyl-2-propanol and 1.35 mmol of 4-methylmorpholine-N-oxide monohydrate. After stirring for two days at ambient temperature, NaHSO3 solution is added. After stirring for one hour, the reaction mixture is extracted with dichloromethane. The organic phase is dried, filtered and then evaporated under reduced pressure. Chromatography of the residue over silica gel (dichloromethane/methanol: 98/2) allows the expected product to be isolated.

Aufarbeitung

  1. stirringAfter stirring for one hour
  2. extractionthe reaction mixture is extracted with dichloromethane
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto be isolated

Quellen und Nachweise

ORD-Eintrag
ord-e2c95e9457c147e1acc8484d8a83ddb9
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642248B2

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