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 2085814Notes

Reaction equation

HRID 2085814 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>C1C=CC=CC=1>[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

3

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-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of Example 518B (0.79 g, 2.81 mmol) in degassed benzene (100 mL) at room temperature was treated with bis-tricyclohexylphosphine benzylidene ruthenium (IV) dichloride (150 mg), stirred for 18 hours, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10%-25% ethyl acetate/heptane to provide the desired product. MS (DCI(+)) m/e 254 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with 10%-25% ethyl acetate/heptane

Sources & evidence

ORD record
ord-0e0c2f78c6f14d72b102c70df96bd5ce
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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