Tert-butyl 3-oxopiperidine-1-carboxylate → Tert-butyl 3-[1-(3-fluorophenyl)methylidene]piperidine-1-carboxylate

HRID 928080ノート

反応式

HRID 928080 の反応式
[Br-].[F:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+].O=[C:36]1[CH2:41][CH2:40][CH2:39][N:38]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:37]1>C1COCC1.O>[F:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:40]2[CH2:41][CH2:36][CH2:37][N:38]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:39]2)[CH:26]=[CH:27][CH:28]=1

参加物

6

反応物 3

HCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateHCID 10527583Phosphonium, [(3-fluorophenyl)methyl]triphenyl-, bromide2 回HCID 23676156Sodium t-butoxide

生成物 1

HCID 86713375Tert-butyl 3-[1-(3-fluorophenyl)methylidene]piperidine-1-carboxylate収率 48.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

(3-Fluorobenzyltriphenylphosphonium bromide (Intermediate 228, 5.3 g) was added in portions to a solution of sodium tert-butoxide (1.06 g) in anhydrous THF (20 mL) at room temperature and the mixture was stirred for 30 minutes. A solution of tert-butyl 3-oxopiperidine-1-carboxylate (2 g) in anhydrous THF (10 mL) was added dropwise at room temperature and the mixture was stirred for 24 hours. The mixture was diluted with water (100 mL) and extracted with ether (100 mL), washed with brine, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexxane with a gradient of 0-20% to give tert-butyl 3-[1-(3-fluorophenyl)-methylidene]piperidine-1-carboxylate (1.42 g).

後処理

  1. stirringthe mixture was stirred for 24 hours
  2. extractionextracted with ether (100 mL)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexxane with a gradient of 0-20%

出典と根拠

ORDレコード
ord-9b94551b56014567851787861eadf205
出典データセット
uspto-grants-2016_03
特許番号
US09290472B2

反応ノート

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