1-tert-Butyl-4-piperidone → 4-(Bromomethylene)-1-tert-butylpiperidine

HRID 394128

反応式

HRID 394128 の反応式
[Br-].[Br:2][CH2:3][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[C:29]([N:33]1[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]1)([CH3:32])([CH3:31])[CH3:30]>C1COCC1>[Br:2][CH:3]=[C:36]1[CH2:37][CH2:38][N:33]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:34][CH2:35]1

参加物

5

反応物 3

HCID 738401-tert-Butyl-4-piperidoneHCID 2733422Phosphonium, (bromomethyl)triphenyl-, bromide (1:1)HCID 23665647Potassium tert-butoxide

生成物 1

HCID 226480424-(Bromomethylene)-1-tert-butylpiperidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of (bromomethyl)triphenylphosphonium bromide (1.52 g, 3.48 mmol) in dry THF (15 mL) at −78° C. was added potassium tert-butoxide (3.5 mL, 1.0M) slowly. After stirring 20 minutes, 1-tert-butylpiperidin-4-one (COMPOUND PPA-1) (595 mg, 3.83 mmol) in THF (2 mL) was added, and the reaction mixture was warmed up to rt slowly over 2 h. The reaction mixture was quenched with brine, and it was extracted with CH2Cl2. The combined extracts were dried over Na2SO4 then concentrated in vacuo. The crude material was purified by flash chromatography eluting first with hexane then gradually increasing to 5% acetone/hexane to give the title compound. 1H NMR (CDCl3, 500 MHz): δ 5.85 (s, 1H); 2.56 (m, 4H); 2.43 (t, J=5.6 Hz, 2H); 2.28 (t, J=5.6 Hz, 2H); 1.08 (s, 9H).

後処理

  1. customThe reaction mixture was quenched with brine, and it
  2. extractionwas extracted with CH2Cl2
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. concentrationthen concentrated in vacuo
  5. customThe crude material was purified by flash chromatography
  6. washeluting first with hexane
  7. temperaturethen gradually increasing to 5% acetone/hexane

出典と根拠

ORDレコード
ord-f18a93c702b94c3e98826f3451ca491e
出典データセット
uspto-grants-2004_10
特許番号
US06809199B2

関連ノート

読み込み中…