Sodium borohydride → Tert-butyl 2-(4-aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

HRID 2036690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036690
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:20]=[CH:19][C:18]3[N:17]([CH3:21])[C:16]4[CH2:22][CH:23]5[NH:27][CH:26]([C:15]=4[C:14]=3[C:13]=2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:25][CH2:24]5)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+]>CO.[Co](Cl)Cl>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([S:9]([C:12]2[CH:20]=[CH:19][C:18]3[N:17]([CH3:21])[C:16]4[CH2:22][CH:23]5[NH:27][CH:26]([C:15]=4[C:14]=3[C:13]=2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:25][CH2:24]5)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 67085455Tert-butyl 2-(4-cyanophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Produkt 1

HCID 67085186Tert-butyl 2-(4-aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateAusbeute 43,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24288Cobalt(II) chlorideKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of the product of Example 30, step A (92 mg, 0.19 mmol) and cobalt(II) chloride (25 mg, 0.19 mmol) in anhydrous methanol (1.5 mL), cooled to 0° C. was treated with sodium borohydride (22 mg, 0.58 mmol). The reaction mixture was stirred at 0° C. for 2 h then quenched with water and filtered through a celite bed. The filtrate was concentrated in vacuo and extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide) to give tert-butyl 2-(4-aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (40 mg, 43%) as a light-yellow solid: ESI MS m/z 382 [M+H]+

Aufarbeitung

  1. customthen quenched with water
  2. filtrationfiltered through a celite bed
  3. concentrationThe filtrate was concentrated in vacuo
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-36983bd1d21a4deeae86bb0ba91ec509
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575186B2

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