Trifluoroacetic acid → Benzyl 4-(2-chloro-pyridin-3-yl-amino)-piperidine-1-carboxylate

HRID 74488

Reaktionsgleichung

Reaktionsgleichung von HRID 74488
C(O)(C(F)(F)F)=O.[CH2:8]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl:25][C:26]1[C:31]([NH2:32])=[CH:30][CH:29]=[CH:28][N:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(OC(C)C)(=O)C>[Cl:25][C:26]1[C:31]([NH:32][CH:21]2[CH2:22][CH2:23][N:18]([C:16]([O:15][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:17])[CH2:19][CH2:20]2)=[CH:30][CH:29]=[CH:28][N:27]=1

Komponenten

7

Edukt 5

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 805282-Chloro-3-pyridylamineHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 46853853Benzyl 4-(2-chloro-pyridin-3-yl-amino)-piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7915Isopropyl AcetateLösungsmittel

Versuchsvorschrift

560 mL (7.25 mol) TFA were added dropwise at approx. 15° C. to 930 g (3.99 mol) N-benzyloxy carbonyl-4-piperidone and 466 g (3.63 mol) 2-chloro-3-aminopyridine in 9.5 L isopropyl acetate. 922 g (4.35 mol) sodium triacetoxyborohydride were added batchwise. The mixture was stirred until the reaction was complete. At RT the reaction mixture was combined with 860 mL sodium hydroxide solution (2 mol/L). The organic phase was separated off, washed with 5 L water and evaporated down.

Aufarbeitung

  1. customAt RT
  2. customThe organic phase was separated off
  3. washwashed with 5 L water
  4. customevaporated down

Quellen und Nachweise

ORD-Eintrag
ord-a06270afeed240be97e9dcae3d8058fa
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829006B2

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