Sodium cyanoborohydride → tert-butyl 4-(2,3-dihydro-1H-indol-7-yl)piperazine-1-carboxylate

HRID 1371518

Reaktionsgleichung

Reaktionsgleichung von HRID 1371518
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[CH:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+]>C(O)(=O)C.C(Cl)Cl.[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH2:20][CH2:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 2

HCID 5003444Sodium cyanoborohydrideHCID 21070951tert-butyl 4-(1H-indol-7-yl)piperazine-1-carboxylate

Produkt 1

HCID 21070950tert-butyl 4-(2,3-dihydro-1H-indol-7-yl)piperazine-1-carboxylateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

7-(4-t-Butyloxycarbonylpiperazin-1-yl)indole (200 mg, 0.67 mmol) is dissolved in acetic acid (4 mL). To the solution, sodium cyanoborohydride (84 mg, 1.33 mmol) is added. The reaction mixture is stirred for about 2 hours at r.t. The mixture is then diluted with DCM and NaOH (1M) is added. The organic layer is separated, dried and concentrated. The residue is chromatographed on the silica gel and the product containing fractions are combined to give about 93 mg of the 7-(4-t-butyloxycarbonylpiperazin-1-yl)-2,3-dihydroindole (46%).

Aufarbeitung

  1. additionis added
  2. customThe organic layer is separated
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is chromatographed on the silica gel
  6. additionthe product containing fractions

Quellen und Nachweise

ORD-Eintrag
ord-d0406b2b6c834bf7a4c9eaf99970312d
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157463B2

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