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Hydrochloric Acid → 2-(3-Fluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

HRID 2036693
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2036693
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:19]=[CH:18][C:17]3[N:16]([CH3:20])[C:15]4[CH2:21][CH:22]5[NH:26][CH:25]([C:14]=4[C:13]=3[C:12]=2C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[ClH:34]>O1CCOCC1>[ClH:34].[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15]2[CH2:21][CH:22]4[NH:26][CH:25]([C:14]3=2)[CH2:24][CH2:23]4)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 67085414Tert-butyl 2-(3-fluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Produkt 1

HCID 529131012-(3-Fluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The product of step A (105 mg, 0.22 mmol) was treated with a solution of 4 M HCl in dioxane (1.5 mL). After 1.5 h the mixture was concentrated in vacuo and the residue partitioned with saturated sodium bicarbonate solution and chloroform. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 90:9:1 chloroform/methanol/ammonium hydroxide) to give 2-(3-fluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (45 mg, 50%, AUC HPLC 98.8%) as a white solid: mp 240-245° C.; 1H NMR (DMSO-d6, 300 MHz) δ 8.20-8.70 (m, 3H), 7.74-7.81 (m, 2H), 7.59-7.71 (m, 3H), 7.45-7.55 (m, 1H), 5.15-5.24 (m, 1H), 4.31-4.43 (m, 1H), 3.66 (s, 3H), 3.21-3.39 (m, 1H), 2.92 (d, J=16.8 Hz, 1H), 2.12-2.29 (m, 2H), 1.96-2.09 (m, 1H), 1.66-1.80 (m, 1H); ESI MS m/z 371 [M+H]+.

Aufarbeitung

  1. concentrationAfter 1.5 h the mixture was concentrated in vacuo
  2. customthe residue partitioned with saturated sodium bicarbonate solution and chloroform
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, 90:9:1 chloroform/methanol/ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-8f2976ddcde646a5aa04d789023efdb1
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08575186B2

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