4-Methylideneoxane → 3-[(3-Chlorophenyl)ethynyl]-1,8-dioxa-2-azaspiro[4.5]dec-2-ene

HRID 2040877Notes

Reaction equation

HRID 2040877 reaction equation
C1(C#CC2CC3(CCN(C(OC(C)(C)C)=O)CC3)ON=2)C=CC=CC=1.[Cl:26][C:27]1[CH:28]=[C:29]([C:33]#[C:34][CH:35]=[N:36][OH:37])[CH:30]=[CH:31][CH:32]=1.[CH2:38]=[C:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>>[Cl:26][C:27]1[CH:28]=[C:29]([C:33]#[C:34][C:35]2[CH2:38][C:39]3([CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[O:37][N:36]=2)[CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 3

HCID 5489754-MethylideneoxaneHCID 57493807Tert-butyl 3-(phenylethynyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylateHCID 765430563-(3-Chlorophenyl)prop-2-ynal oxime

Product 1

HCID 566442253-[(3-Chlorophenyl)ethynyl]-1,8-dioxa-2-azaspiro[4.5]dec-2-ene

Procedure

The title compound was prepared following the procedure described for Compound 1b, using Compound 31e instead of Compound 1a and 4-methylenetetrahydropyran (Tetrahedron, 46(7), 2411-2424, 1990) instead of tert-butyl 4-methylenepiperidine-1-carboxylate. After the usual work-up procedure, the residue was purified by means of automated flash chromatography (SP1 ®TM-Biotage; gradient Petroleum Ether-EtOAc from 10:1 to 8:2) to give the title compound as a yellowish solid. Yield: 23.7%.

Workup

  1. customThe title compound was prepared
  2. customAfter the usual work-up procedure, the residue was purified by means of automated flash chromatography (SP1 ®TM-Biotage; gradient Petroleum Ether-EtOAc from 10:1 to 8:2)

Sources & evidence

ORD record
ord-fcd3b2e854de4ca28ae105cee4ba8b22
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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