1,2-Dichloroethane → tert-Butyl 3-(1-Pivaloyl-1H-indazol-5-ylamino)piperidine-1-carboxylate

HRID 1911991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1911991
O=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.ClCCCl.C(O)(=O)/C=C\C(O)=O.[NH2:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[N:33]([C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[N:32]=[CH:31]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)(O)[O-].[Na+]>[C:37]([N:33]1[C:34]2[C:30](=[CH:29][C:28]([NH:27][CH:2]3[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]3)=[CH:36][CH:35]=2)[CH:31]=[N:32]1)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 66716091HCID 66716091, Verbindung

Produkt 1

HCID 59799788tert-Butyl 3-(1-Pivaloyl-1H-indazol-5-ylamino)piperidine-1-carboxylateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Into a 1 L 3-neck round bottom flask fitted with a nitrogen inlet and mechanical stirrer was added tert-butyl 3-oxopiperidine-1-carboxylate (14.2 g, 0.07 mol), 1,2-dichloroethane (300 mL), and 1-(5-amino-1H-indazol-1-yl)-2,2-dimethylpropan-1-one maleate salt (23.0 g, 0.07 mol). The vessel was purged with nitrogen and stirred at 20° C. for one hour. Sodium triacetoxyborohydride (19.0 g, 0.09 mol) was added, and the reaction was monitored by analytical TLC to completion. The reaction was diluted with 100 mL of saturated sodium bicarbonate. The organic phase was isolated, dried over MgSO4, filtered and evaporated to dryness to afford the title compound as a yellow solid (25.0 g, 91%).

Aufarbeitung

  1. customInto a 1 L 3-neck round bottom flask fitted with a nitrogen inlet and mechanical stirrer
  2. customThe vessel was purged with nitrogen
  3. customThe organic phase was isolated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9fbb86af749941089a178d466d775f55
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604218B2

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