Acetic Acid → HCID 57494025, Verbindung

HRID 888945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 888945
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][CH2:16][O:17][CH3:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH:24]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH2:15][CH2:16][O:17][CH3:18])[CH2:24][C:20]2[S:19][CH:23]=[CH:22][N:21]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 27349031,3-Thiazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 43652134tert-Butyl 4-[(2-methoxyethyl)amino]piperidine-1-carboxylate

Produkt 1

HCID 57494025HCID 57494025, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 4-(2-methoxy-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester (465 mg), and 2-thiazolecarboxaldehyde (190 μl) stirring in anhydrous 1,2-dichloroethane (5 ml) was added glacial acetic acid (1 equiv.) and sodium triacetoxyborohydride (458 mg). The reaction mixture was stirred for 12 hours at room temperature, then diluted with dichloromethane (40 ml), washed with brine, dried (MgSO4) and the solvents removed in vacuo. The residue was purified using flash silica chromatography to give 4[(2-methoxy-ethyl)-thiazol-2-ylmethyl-amino]-piperidine-1-carboxylic acid tert-butyl ester (574 mg). Treatment of this compound with HCl in dichloromethane/methanol and a basic wash with sodium hydrogen carbonate yielded (2-methoxy-ethyl)-piperidin-4-yl-thiazol-2-ylmethyl-amine.

Aufarbeitung

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. customthe solvents removed in vacuo
  4. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-91b81e0e2d4f4ab0a90905960dd6df27
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252792B2

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