Nitrogen → HCID 59382877, Verbindung

HRID 2266205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2266205
N#N.[F:3][C:4]([F:21])([F:20])[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)=[O:6].C(=O)=O.CC(C)=O.[CH3:29][O:30][CH2:31][CH2:32][CH2:33][CH2:34][Mg]Cl.[NH4+].[Cl-]>C(OCC)C.C1COCC1>[F:21][C:4]([F:3])([F:20])[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:8]1)([OH:6])[CH2:34][CH2:33][CH2:32][CH2:31][O:30][CH3:29]

Komponenten

8

Edukt 5

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 18522661Acetone cardiceHCID 49759206tert-Butyl 3-(trifluoroacetyl)piperidine-1-carboxylateHCID 178495008HCID 178495008, Verbindung

Produkt 1

HCID 59382877HCID 59382877, VerbindungAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Under protection of N2 gas, tert-butyl 3-(2,2,2-trifluoroacetyl)piperidine-1-carboxylate (102 mg, 0.363 mmol) was dissolved dry THF (8 mL) and cooled to −78° C. (dry ice/acetone bath). 1.22 M methoxybutylmagnesium chloride in THF (600 μL, 2 equiv) solution was added slowly. After 10 min, the reaction was allowed to warm up to rt slowly. After 2 h, satd aq NH4Cl (15 mL) solution was added to the reaction mixture. The mixture was diluted with diethyl ether and the layers were separated. The aqueous layer was extracted with diethyl ether (3×10 mL). The combined organic layers were washed with brine (10 mL) and dried over Na2SO4. After concentration, the crude product was purified by prep HPLC to afford tert-butyl 3-(1,1,1-trifluoro-2-hydroxy-6-methoxyhexan-2-yl)piperidine-1-carboxylate (20 mg, 15%).

Aufarbeitung

  1. waitAfter 2 h
  2. additionwas added to the reaction mixture
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with diethyl ether (3×10 mL)
  5. washThe combined organic layers were washed with brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationAfter concentration
  8. customthe crude product was purified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c2ade8266a2c4a82be88e2bf3ed9b2c8
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858624B2

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