tert-Butyl 2-(2,2-dibromoethenyl)pyrrolidine-1-carboxylate → tert-Butyl 2-ethynylpyrrolidine-1-carboxylate

HRID 354274

Reaktionsgleichung

Reaktionsgleichung von HRID 354274
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]=[C:14](Br)Br)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]#[CH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 14730280tert-Butyl 2-(2,2-dibromoethenyl)pyrrolidine-1-carboxylateHCID 178418339Butyllithium

Produkt 1

HCID 14730283tert-Butyl 2-ethynylpyrrolidine-1-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred cold (minus 78° C.) solution of 1-(tert-butoxycarbonyl)-2-(2,2-dibromoethenyl)pyrrolidine (7.81 g, 22 mmol) in THF (200 mL) was added n-BuLi (1.59 M in hexane, 28 mL, 44 mmol) over 10 min. and the stirring was continued for 2 hr at the same temp. The reaction was quenched by the addition of sat. NH4Cl and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, and evaporated. The residue was chromatographed on silica-gel with n-hexane-AcOEt (10:1, v/v) as eluent to give 4.15 g (97%) 1-(tert-butoxycarbonyl)-2-ethynyl pyrrolidine as a light yellow oil. 1H-NMR (CDCl3) δ1.48 (9 H, s), 1.82-2.21 (4 H, m), 3.30-3.45 (2 H, m), 4.41-4.52 (1 H, m).

Aufarbeitung

  1. customThe reaction was quenched by the addition of sat. NH4Cl
  2. extractionextracted with EtOAc
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was chromatographed on silica-gel with n-hexane-AcOEt (10:1

Quellen und Nachweise

ORD-Eintrag
ord-6076674b8c2e46b9bd8735b53ecc9621
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756378B2

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