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

HRID 350336

반응식

HRID 350336 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred cold (minus 78° C.) solution of l-(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) δ 1.48 (9 H, s), 1.82–2.21 (4 H, m), 3.30–3.45 (2 H, m), 4.41–4.52 (1 H, m).

후처리

  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

출처 및 근거

ORD 기록
ord-c5fc05279806464ab9692418dd144daf
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179819B2

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