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

HRID 394128

반응식

HRID 394128 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f18a93c702b94c3e98826f3451ca491e
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809199B2

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