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Methyl morpholine oxide → Methyl (5r,6s)-rel-13-cyclohexyl-6,7-dihydro-5,6-dihydroxy-5h-indolo[2,1-a][2]benzazepine-10-carboxylate

HRID 860739
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 860739
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:25]([O:27][CH3:28])=[O:26])=[CH:12][C:13]=3[N:14]3CC=C[C:17]4[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[N+]1([O-])CC[O:33]CC1.[CH3:37][C:38]([CH3:40])=[O:39].O>S([O-])([O-])(=O)=S.[Na+].[Na+].O=[Os](=O)(=O)=O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:25]([O:27][CH3:28])=[O:26])=[CH:12][C:13]=3[N:14]3[CH2:40][C@H:38]([OH:39])[C@H:37]([OH:33])[C:17]4[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
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Komponenten

6

Edukt 3

HCID 82029Methyl morpholine oxideHCID 11667856methyl 13-cyclohexyl-7H-indolo[2,1-a][2]benzazepine-10-carboxylateHCID 18366337Propan-2-one--water (1/1)

Produkt 1

HCID 69207219Methyl (5r,6s)-rel-13-cyclohexyl-6,7-dihydro-5,6-dihydroxy-5h-indolo[2,1-a][2]benzazepine-10-carboxylateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318
Osmium Tetroxide
Katalysator
HCID 24477Sodium ThiosulfateLösungsmittel

Versuchsvorschrift

OsO4 (23 mg, 0.09 mmol) was added to a stirred solution of methyl 13-cyclohexyl-7H-indolo{2,1-a][2]benzazepine-10-carboxylate (341 mg, 0.92 mmol) and 4-methyl-morpholine N-oxide(430 mg, 3.68 mmol) in acetone-water (50 mL-6 mL) at rt. The reaction mixture was stirred at rt for 18 hr and then diluted with aqueous sodium thiosulfate. The mixture was extracted with ethyl acetate. The organic layer was washed with brine (3×) and dried over sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified utilizing a Biotage apparatus with a prepacked silica column and using gradients of hexanes:ethyl acetate of from (98:2) to (80:20) to afford the product as a light yellow solid (340 mg, 91%). ESI-MS m/z 406 (MH+); 1H NMR (500 MHz, MeOD) δ 1.25 (m, 1 H) 1.43 (m, 2 H) 1.58 (d, J=13.12 Hz, 1 H) 1.77 (d, J=8.85 Hz, 2 H) 2.02 (m, 4 H) 2.93 (m, 1 H) 3.31 (m, 1 H) 3.93 (s, 3 H) 4.40. (d, J=4.58 Hz, 1 H) 4.52 (m, 1 H) 4.68 (dd, J=14.19, 7.17 Hz, 1 H) 7.40 (t, J=7.32 Hz, 1 H) 7.44 (t, J=7.32 Hz, 1 H) 7.51 (t, J=7.48 Hz, 1 H) 7.70 (d, J=8.55 Hz, 1 H) 7.78 (d, J=7.63 Hz, 1 H) 7.86 (d, J=8.55 Hz, 1 H) 8.15 (s, 1 H).

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine (3×)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-39ac5afe6e384f05ae655de3decc42b6
Quelldatensatz
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07153848B2

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