1,4-Dioxaspiro[4.5]decan-8-one → 8-Methylidene-1,4-dioxaspiro[4.5]decane

HRID 2040860Notes

Reaction equation

HRID 2040860 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6]N(C2C([N+]([O-])=O)=CC=CN=2)[CH2:4][CH2:3]1.[Li].C[Si]([N-][Si](C)(C)C)(C)C.[Li].[O:28]1[C:32]2(CCC(=O)CC2)[O:31][CH2:30][CH2:29]1.[N+](C1C(N2CCC(=O)CC2)=NC=CC=1)([O-])=O>>[CH2:1]=[C:2]1[CH2:3][CH2:4][C:32]2([O:31][CH2:30][CH2:29][O:28]2)[CH2:6][CH2:7]1

Participants

6

Reactant 5

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 3028194LithiumHCID 35105401-(3-Nitropyridin-2-yl)piperidin-4-oneHCID 574938092-(4-Methylene-1-piperidyl)-3-nitropyridineHCID 86605622Lithium bistrimethylsilylamide

Product 1

HCID 109537438-Methylidene-1,4-dioxaspiro[4.5]decane

Procedure

The title compound was prepared following the method reported here for Compound 2a, but using lithium-bis-trimethylsilylamide instead of buthyl lithium and carrying out the reaction at −20° C. As starting material 1,4-dioxaspiro[4.5]decan-8-one replaced 1-(3-nitro-2-pyridyl)-4-oxopiperidine. After the usual work-up procedure the residue was purified by means of automated flash chromatography (Horizon®TM-Biotage; Petroleum Ether EtOAc 95:5) to give the title compound as fluid colourless oil. Yield: 99.3%.

Workup

  1. customThe title compound was prepared
  2. customthe reaction at −20° C
  3. customAfter the usual work-up procedure the residue was purified by means of automated flash chromatography (Horizon®TM-Biotage; Petroleum Ether EtOAc 95:5)

Sources & evidence

ORD record
ord-f3699746ad754c4499ad5b4d69347e4b
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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