Isopropyl 4-Hydroxypiperidine-1-carboxylate → HCID 86597364, Verbindung

HRID 1036793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036793
Cl[C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.[CH:11]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]1)=[O:16])([CH3:13])[CH3:12].CC(C)([O-])C.[K+]>C1COCC1>[CH:11]([O:14][C:15]([N:17]1[CH2:18][CH2:19][CH:20]([O:23][C:2]2[C:7]([CH2:8][CH3:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=2)[CH2:21][CH2:22]1)=[O:16])([CH3:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 16745126Isopropyl 4-Hydroxypiperidine-1-carboxylateHCID 218284324,6-Dichloro-5-ethylpyrimidineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 86597364HCID 86597364, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4,6-dichloro-5-ethyl-pyrimidine (1 g, 5.65 mmol) and 4-hydroxy-piperidine-1-carboxylic acid isopropyl ester (1.05 g, 5.65 mmol) in dry THF under nitrogen at 0° C., potassium tert-butoxide (1M solution in THF, 6.78 mL) was added dropwise. The reaction was stirred at rt for 30 min. The mixture was quenched with water and extracted with EtOAc (3×). The organic layer was washed with water, sat. NH4Cl and brine, followed by drying over sodium sulfate and concentration under vacuo. The resulting oil was purified by HPLC to afford 4-(6-chloro-5-ethyl-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester (0.74 g, 39.8%) as a colorless oil. Exact mass calculated for C15H22ClN3O3 327.13, found 328.2 (MH+).

Aufarbeitung

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc (3×)
  3. washThe organic layer was washed with water, sat. NH4Cl and brine
  4. dry with materialby drying over sodium sulfate and concentration under vacuo
  5. customThe resulting oil was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e2789ecc7188474b801163ef269f9a81
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546429B2

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