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 2213036Notes

Reaction equation

HRID 2213036 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 60145889Benzylidene-bis(triphenylphosphine)ruthenium dichlorideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5aabd353284941e6b687a5ad0c28d942
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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