Acetic Acid → Tert-butyl 4-((6-bromopyridin-3-yl)amino)piperidine-1-carboxylate

HRID 1467963

Reaktionsgleichung

Reaktionsgleichung von HRID 1467963
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Br:15][C:16]1[N:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(OCC)(=O)C>[Br:15][C:16]1[N:21]=[CH:20][C:19]([NH:22][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)=[CH:18][CH:17]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 6428116-Bromopyridin-3-amineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 86602140Tert-butyl 4-((6-bromopyridin-3-yl)amino)piperidine-1-carboxylateAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 63651,1-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of tert-butyl 4-oxopiperidine-1-carboxylate (1.15 g, 5.78 mmol) and 6-bromopyridin-3-amine (0.5 g, 2.89 mmol) in dichloroethane (20 mL), acetic acid (8 mL, 2.89 mmol) was added and the contents were stirred at room temperature for 3 h. Sodium triacetoxy borohydride (1.225 g, 5.78 mmol) was added and the contents were stirred at room temperature for 12 h. The reaction was diluted with ethyl acetate and washed with brine; the organic layer was separated and concentrated in vacuo. The resulting residue was purified by flash column chromatography to give tert-butyl 4-((6-bromopyridin-3-yl)amino)piperidine-1-carboxylate (0.638 g, 62%); MS: 357.1 (M+1)

Aufarbeitung

  1. additionwas added
  2. stirringthe contents were stirred at room temperature for 12 h
  3. washwashed with brine
  4. customthe organic layer was separated
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-095a9df2de08454da67543e86e1307a9
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000175B2

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