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 2213036ノート

反応式

HRID 2213036 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 60145889Benzylidene-bis(triphenylphosphine)ruthenium dichloride触媒HCID 6344Dichloromethane溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5aabd353284941e6b687a5ad0c28d942
出典データセット
uspto-grants-2006_09
特許番号
US07105507B2

反応ノート

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