Triphenylphosphine → Tert-butyl 4-[bromo(fluoro)methylidene]piperidine-1-carboxylate

HRID 1895971ノート

反応式

HRID 1895971 の反応式
O=[C:2]1[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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34][C:35](Br)(Br)[F:36].C([Zn]CC)C>C1COCC1>[Br:34][C:35]([F:36])=[C:2]1[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

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 67707TribromofluoromethaneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178418750HCID 178418750、化合物

生成物 1

HCID 68795703Tert-butyl 4-[bromo(fluoro)methylidene]piperidine-1-carboxylate収率 44%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (500 mg, 2.52 mmol), triphenylphosphine (808 mg, 3.02 mmol) and tribromofluoromethane (818 mg, 3.02 mmol) in 50 mL of anhydrous THF was added dropwise a solution of diethylzinc (1 M in hexane, 3.02 mL, 3.02 mmol) stirring at r.t. After 2.5 h, the reaction mixture was quenched with MeOH (10 mL), stirred for 30 min., evaporated to dryness in vacuo. Purification was carried out by automated flash liquid chromatography (Horizon™-Biotage) eluting with Petroleum Ether-EtOAc gradient from 95:5:0 to 90:10 to afford the title compound (326 mg).

後処理

  1. customthe reaction mixture was quenched with MeOH (10 mL)
  2. stirringstirred for 30 min.
  3. customevaporated to dryness in vacuo
  4. customPurification
  5. washeluting with Petroleum Ether-EtOAc gradient from 95:5:0 to 90:10

出典と根拠

ORDレコード
ord-8a20775d1b9a4a04acddf43d695a702e
出典データセット
uspto-grants-2013_08
特許番号
US08518916B2

反応ノート

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