1,1-Dimethylethyl 4-(2-propen-1-yl)-4-(2-propen-1-yloxy)-1-piperidinecarboxylate → Tert-butyl 1-oxa-9-azaspiro[5.5]undec-3-ene-9-carboxylate

HRID 2213036노트

반응식

HRID 2213036 반응식
[CH2:1]([C:4]1([O:17][CH2:18][CH:19]=[CH2:20])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)C=C>ClCCl.C=CC1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ru]Cl>[O:17]1[C:4]2([CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:8][CH2:9]2)[CH2:1][CH:20]=[CH:19][CH2:18]1

참가 물질

4

반응물 1

HCID 219552731,1-Dimethylethyl 4-(2-propen-1-yl)-4-(2-propen-1-yloxy)-1-piperidinecarboxylate

생성물 1

HCID 21955282Tert-butyl 1-oxa-9-azaspiro[5.5]undec-3-ene-9-carboxylate수율 75%

시약·촉매·용매 2

HCID 60145889Benzylidene-bis(triphenylphosphine)ruthenium dichloride촉매HCID 6344Dichloromethane용매3회

실험 절차

Solutions of 1,1-dimethylethyl 4-(2-propenyl)-4-(2-propenyloxy)-1-piperidinecarboxylate (Description 130, 4.9 g, 17.4 mmol) in dichloromethane (1.2 L) and bis(tricyclohexylphosphine)benzylidine ruthenium (IV) dichloride (717 mg, 0.87 mmol) in dichloromethane (1.2 L) were added dropwise simultaneously to dichloromethane (600 mL) over a period of 8 hours, and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with 9:1 isohexane:ethyl acetate, to give the title compound (3.3 g, 75%). m/z (ES+) 254 (M+1).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by flash column chromatography on silica gel
  3. washeluting with 9:1 isohexane

출처 및 근거

ORD 기록
ord-5aabd353284941e6b687a5ad0c28d942
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07105507B2

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