Tert-butyl 4-(3,3-dibromoallyl)piperidine-1-carboxylate → Tert-butyl 4-(prop-2-yn-1-yl)piperidine-1-carboxylate

HRID 278215

Reaktionsgleichung

Reaktionsgleichung von HRID 278215
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]=[C:16](Br)Br)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]#[CH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 15503387Tert-butyl 4-(3,3-dibromoallyl)piperidine-1-carboxylateHCID 178418339Butyllithium

Produkt 1

HCID 18187546Tert-butyl 4-(prop-2-yn-1-yl)piperidine-1-carboxylateAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 118 mg (0.31 mmol) of 1-(t-butoxycarbonyl)-4-(3,3-dibromoprop-2-en-1-yl)piperidine from Step A in THF (4 mL) at −78° C. was added a 2.5M solution of n-butyl lithium (0.370 mL, 0.92 mmol). After stirring at −78° C. for 45 min, the reaction mixture was quenched with sat'd ammonium chloride (4 mL) and diluted with ether (25 mL). After separating the phases, the aqueous layer was extracted with ether. The combined organic phases were washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by FC (4:1 v/v hexanes/ether) to give the title compound (55 mg).

Aufarbeitung

  1. customthe reaction mixture was quenched with sat'd ammonium chloride (4 mL)
  2. additiondiluted with ether (25 mL)
  3. customAfter separating the phases
  4. extractionthe aqueous layer was extracted with ether
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by FC (4:1 v/v hexanes/ether)

Quellen und Nachweise

ORD-Eintrag
ord-f06c6eac3a3f4a698660b3098e5a9c4b
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358979B1

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