8-Methylenespiro[4.5]decane → 3-[(3-Methylphenyl)ethynyl]-1-oxa-2-azadispiro[4.2.4.2]tetradec-2-ene

HRID 2040890Notes

Reaction equation

HRID 2040890 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]#[C:5][C:6]1[CH:7]=[C:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1.[CH2:14]=[C:15]1[CH2:24][CH2:23][C:18]2([CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:17][CH2:16]1>>[CH3:12][C:8]1[CH:7]=[C:6]([C:5]#[C:4][C:3]2[CH2:14][C:15]3([CH2:16][CH2:17][C:18]4([CH2:19][CH2:20][CH2:21][CH2:22]4)[CH2:23][CH2:24]3)[O:1][N:2]=2)[CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 574938568-Methylenespiro[4.5]decaneHCID 86662877N-hydroxy-3-(m-tolyl)prop-2-ynimidoyl chloride

Product 1

HCID 566444373-[(3-Methylphenyl)ethynyl]-1-oxa-2-azadispiro[4.2.4.2]tetradec-2-ene

Procedure

The title compound was prepared following the procedure described for Compound 3c, using Compound 91d instead of Compound 3b and Compound 89a instead of Compound 3a. After the usual work-up procedure, the residue was purified by means of automated flash chromatography (ISOLERA®TM-Biotage; gradient Petroleum Ether-EtOAc from 97:3 to 9:1) to give the title compound as a white-yellowish solid. Yield: 55.8%.

Workup

  1. customThe title compound was prepared
  2. customAfter the usual work-up procedure, the residue was purified by means of automated flash chromatography (ISOLERA®TM-Biotage; gradient Petroleum Ether-EtOAc from 97:3 to 9:1)

Sources & evidence

ORD record
ord-6163f8e566004cc097db5b08b8600e4e
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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