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

HRID 350336

反応式

HRID 350336 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 14730283tert-Butyl 2-ethynylpyrrolidine-1-carboxylate収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c5fc05279806464ab9692418dd144daf
出典データセット
uspto-grants-2007_02
特許番号
US07179819B2

関連ノート

読み込み中…