Acetic Acid → tert-Butyl 4-(3-fluoroanilino)piperidine-1-carboxylate

HRID 43339

Reaktionsgleichung

Reaktionsgleichung von HRID 43339
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.[F:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[F:15][C:16]1[CH:17]=[C:18]([NH:19][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:20]=[CH:21][CH:22]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 97423-FluoroanilineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 23137591tert-Butyl 4-(3-fluoroanilino)piperidine-1-carboxylateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1,1-dimethylethyl 4-oxo-1-piperidinecarboxylate (1.91 g, 9.53 mmol), 3-fluoroaniline (1.06, 9.53 mmol) and acetic acid (0.55 ml, 9.53 mmol) in 1,2-DCE (50 ml) was stirred at room temperature overnight. Sodium tri(acetoxy)borohydride (2.82 g, 13.3 mmol) was then added, stirred for 8 hrs and then allowed to stand at room temperature. The reaction mixture was diluted with DCM and washed with NaHCO3 solution, dried over MgSO4 and then concentrated to give the product which was purified by column chromatography. Elution with 0-40% EtOAc/pentane gave the title compound as a white solid (2.3 g). δH (CDCl3, 250 MHz) 7.08 (1H, q), 6.35 (3H, m), 4.04 (1H, br s), 3.65 (1H, br s), 3.38 (1H, m), 2.92 (2H, m), 2.02 (2H, m), 1.47 (9H, s), 1.34 (2H, m).

Aufarbeitung

  1. customto stand at room temperature
  2. washwashed with NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give the product which
  6. customwas purified by column chromatography
  7. washElution with 0-40% EtOAc/pentane

Quellen und Nachweise

ORD-Eintrag
ord-ed5e4844a6594da5b9d1c7dabd6a94e7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536182B2

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