Dimethyl Sulfoxide → Benzyl 4-methylidenepiperidine-1-carboxylate

HRID 1781998

반응식

HRID 1781998 반응식
[H-].[Na+].O=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1.O.[CH3:21]S(C)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:21]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1

참가 물질

6

반응물 4

HCID 679Dimethyl Sulfoxide3회HCID 962WaterHCID 24758Sodium hydrideHCID 643496Benzyl 4-oxopiperidine-1-carboxylate

생성물 1

HCID 15519136Benzyl 4-methylidenepiperidine-1-carboxylate

시약·촉매·용매 1

HCID 74505Methyltriphenyliphosphonium bromide촉매

반응 조건

온도
60 °C

실험 절차

A sodium hydride (13.2 g) was added to an anhydrous dimethylsulfoxide (176 mL) and the mixture was heated for 2 hours at 60° C. After cooling, to a suspension of methyltriphenylphosphonium bromide (110.4 g) in dimethylsulfoxide (120 mL) was added the reaction mixture, and the mixture was stirred for 30 minutes at room temperature. To the reaction mixture was added a solution of benzyl 4-oxo-1-piperidinecarboxylate (60 g) in dimethylsulfoxide (150 mL), the mixture was stirred for 1 hour at 50° C. After cooling, to the mixture was added water (2.5 L) and the mixture was extracted with ethyl acetate (1.5 L). The organic layer was washed with a saturated aqueous solution of ammonium chloride (0.5 L) and a saturated aqueous solution of sodium chloride (0.5 L), dried and then concentrated. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate:chloroform=9:1:1) to give the title compound (51.1 g) having the following physical data.

후처리

  1. additionwas added the reaction mixture
  2. stirringthe mixture was stirred for 1 hour at 50° C
  3. temperatureAfter cooling, to the mixture
  4. extractionthe mixture was extracted with ethyl acetate (1.5 L)
  5. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride (0.5 L)
  6. dry with materiala saturated aqueous solution of sodium chloride (0.5 L), dried
  7. concentrationconcentrated
  8. customThe obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate:chloroform=9:1:1)

출처 및 근거

ORD 기록
ord-976196165fb343849eb72f934f0676e2
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07498323B2

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