Sodium Thiosulfate → ethyl 3-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)benzoate

HRID 1876923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876923
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:20]=2[CH:19]=[C:18]2[C@@:13]([CH3:34])([C@@H:14]([CH:21]([OH:33])[C:22]4[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=4)[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:15][CH2:16][CH2:17]2)[CH2:12]3)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:20]=2[CH:19]=[C:18]2[C@@:13]([CH3:34])([C@@H:14]([C:21]([C:22]4[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=4)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:33])[CH2:15][CH2:16][CH2:17]2)[CH2:12]3)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67447028ethyl 3-(((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinolin-6-yl)(hydroxy)methyl)benzoate

Produkt 1

HCID 67445249ethyl 3-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The above ethyl 3-(((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinolin-6-yl)(hydroxy)methyl)benzoate was dissolved in anhydrous methylene chloride (5 mL). Pyridine (0.1 mL) and Dess-Martin periodinane (215 mg, 0.51 mmol) were added. The reaction mixture was stirred at RT for 40 min before saturated aqueous sodium bicarbonate solution (6 mL) and saturated aqueous sodium thiosulfate solution (3 mL) were added. The mixture was stirred at RT for 20 min. The aqueous layer was separated and extracted with methylene chloride (2×2 mL). The combined organic solutions were dried (Na2SO4). Silica gel flash chromatography (20-100% ethyl acetate in heptanes, then 0-20% methanol in ethyl acetate) gave ethyl 3-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)benzoate as a solid.

Aufarbeitung

  1. additionwere added
  2. customThe aqueous layer was separated
  3. extractionextracted with methylene chloride (2×2 mL)
  4. dry with materialThe combined organic solutions were dried (Na2SO4)

Quellen und Nachweise

ORD-Eintrag
ord-429013e3bce1449aa0a08d1c96a5881c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309730B2

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