Dichloromethane → (S)-{2-[6-(4-Methoxy-phenyl)-2,3-dihydro-indol-1-yl]-1-methyl-ethyl}-carbamic-Acid Tert-Butyl Ester

HRID 1716536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1716536
[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([CH3:27])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:17]=2)[CH:12]=[CH:11]1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[BH3-]C#N.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([CH3:27])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:17]=2)[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 67031552(S)-{2-[6-(4-Methoxy-phenyl)-indol-1-yl]-1-methyl-ethyl}-carbamic acid tert-butyl ester

Produkt 1

HCID 20761960(S)-{2-[6-(4-Methoxy-phenyl)-2,3-dihydro-indol-1-yl]-1-methyl-ethyl}-carbamic-Acid Tert-Butyl EsterAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(S)-{2-[6-(4-Methoxy-phenyl)-indol-1-yl]-1-methyl-ethyl}-carbamic acid tert-butyl ester (1.80 g) was dissolved in acetic acid (25 mL) and CH2Cl2 (10 mL) and cooled to 0° C. NaCNBH3 (1.41 g) was added in portions and the resulting mixture was allowed to stir for 4 hours. The reaction mixture was diluted with ethyl acetate and extracted with concentrated NaOH solution. The organic layer washed with brine, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (gradient of ethyl acetate in hexanes) to give the title compound as a brown oil (1.7 g).

Aufarbeitung

  1. extractionextracted with concentrated NaOH solution
  2. washThe organic layer washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography (gradient of ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-eff75cf5657d4db982bad1d17b9ff0d0
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803819B2

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