Methyl iodide → Tert-butyl 4-methyl-4-(methylthio)piperidine-1-carboxylate

HRID 524912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 524912
[CH3:1][C:2]1([SH:15])[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.[Li+].[CH3:17][Si]([N-][Si](C)(C)C)(C)C.CI>C1COCC1>[CH3:1][C:2]1([S:15][CH3:17])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 71629631tert-Butyl 4-mercapto-4-methylpiperidine-1-carboxylate

Produkt 1

HCID 86720965Tert-butyl 4-methyl-4-(methylthio)piperidine-1-carboxylateAusbeute 96,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of tert-butyl 4-methyl-4-sulfanyl-piperidine-1-carboxylate (380 mg, 1.642 mmol) in THF (5 mL) cooled to −78° C. was added LiHMDS (1.724 mL of 1 M, 1.724 mmol) and the solution stirred for 10 mins before MeI (256.3 mg, 0.1124 mL, 1.806 mmol) was added and the solution allowed to warm to 0° C. over approximately 1 h. The reaction was then quenched carefully by the addition of saturated ammonium chloride and extracted into EtOAc. The aqueous was further extracted with EtOAc and the combined organics were washed with brine, dried (MgSO4) and concentrated to give a yellow oil (390 mg, 96%).

Aufarbeitung

  1. additionwas added
  2. customThe reaction was then quenched carefully by the addition of saturated ammonium chloride
  3. extractionextracted into EtOAc
  4. extractionThe aqueous was further extracted with EtOAc
  5. washthe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-459917c0919c488ea286fe7c65a8439b
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340546B2

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