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Trifluoroacetic acid → ethyl 6-[(ethoxycarbonyl)amino]-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate

HRID 1267069
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Reaktionsgleichung

Reaktionsgleichung von HRID 1267069
[CH2:1]([O:3][C:4]([NH:6][C:7]1[C:15]2[NH:14][C:13]3[CH2:16][CH2:17][N:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][C:12]=3[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:5])[CH3:2].C(O)(C(F)(F)F)=O.[BH3-]C#N.[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([NH:6][C:7]1[C:15]2[NH:14][CH:13]3[CH2:16][CH2:17][N:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][CH:12]3[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:5])[CH3:2]
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Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 22036763ethyl 6-[(ethoxycarbonyl)amino]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Produkt 1

HCID 22036764ethyl 6-[(ethoxycarbonyl)amino]-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of ethyl 6-[(ethoxycarbonyl)amino]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b] indole-2-carboxylate (4.5 g, 13.6 mmol) in CH2Cl2 (40 mL) at 0° C. was added TFA (20 mL) followed by NaCNBH3 (1.8 g, 27 mmol) and stirred at rt for 3 hours before the solvent was removed by the nitrogen stream. To the resulting residue were added CH2Cl2 (40 mL) and 6N HCl (20 mL) and stirred for 0.5 hour. The solution was diluted with water (20 mL), 1N NaOH (30 mL) and extracted with CH2Cl2 (2×30 mL). The combined extracts were dried over magnesium sulfate, concentrated, and purified by flash chromatography to afford ethyl 6-[(ethoxycarbonyl)amino]-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate (3.6 g, 80%) as a clear oil. MS [M+H]+334. 1H NMR (CDCl3, 300 MHz): δ 6.97 (d, 1H, J=7.3 Hz), 6.85 (d, 1H, J=7.3 Hz), 6.72 (t, 1H, J=7.3 Hz), 4.05 (m, 4H), 3.41 (m, 4H), 1.92 (m, 2H), 1.20-1.24 (m, 6H) ppm.

Aufarbeitung

  1. customwas removed by the nitrogen stream
  2. additionTo the resulting residue were added CH2Cl2 (40 mL) and 6N HCl (20 mL)
  3. stirringstirred for 0.5 hour
  4. additionThe solution was diluted with water (20 mL), 1N NaOH (30 mL)
  5. extractionextracted with CH2Cl2 (2×30 mL)
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. concentrationconcentrated
  8. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1513cb945bf44e9eb8c05595a0a6a376
Quelldatensatz
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06552017B1

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