1,5-Dioxaspiro[5.5]undecan-9-one → 9-Methylidene-1,5-dioxaspiro[5.5]undecane

Reaction equation

[CH2:1]=C1CN(C(OC(C)(C)C)=O)C1.[CH2:13]1[C:18]2([O:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH2:17][CH2:16][C:15](=O)[CH2:14]1>>[CH2:1]=[C:15]1[CH2:16][CH2:17][C:18]2([O:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH2:13][CH2:14]1

Participants

Reactant 2

HCID 103133001,5-Dioxaspiro[5.5]undecan-9-one

HCID 55269097tert-Butyl 3-methylideneazetidine-1-carboxylate

Product 1

HCID 574938609-Methylidene-1,5-dioxaspiro[5.5]undecane

Procedure

The title compound was prepared following the methodology described for Compound 28a replacing 1-Boc-3-azetidinone with 7,11-dioxaspiro[5.5]undecan-3-one. After the usual work-up procedure, the residue was purified by means of automated flash chromatography (SP01®TM-Biotage; Et2O) to give the title compound as a pale-yellow oil. Yield: 96.3%.

Workup

customThe title compound was prepared
customAfter the usual work-up procedure, the residue was purified by means of automated flash chromatography (SP01®TM-Biotage; Et2O)

Sources & evidence

ORD record: ord-7ed4c19434d44a6b98126ccf2a6640a8
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580962B2

Reaction notes

Loading…