tert-Butyl methacrylate → HCID 66653601, compound

HRID 588251Notes

Reaction equation

[CH3:1][C:2]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[O:16][CH2:15][CH2:14][NH:13][CH2:12]2)=[CH:7][CH:6]=1.[C:22]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:26])[C:23]([CH3:25])=[CH2:24].N12CCCN=C1CCCCC2>CN(C=O)C>[C:28]([O:27][C:22](=[O:26])[CH:23]([CH3:25])[CH2:24][N:13]1[CH2:14][CH2:15][O:16][CH:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][C:3]3[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:2]=3[CH3:1])=[CH:10][CH:9]=2)[CH2:12]1)([CH3:31])([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-[4-(2,3-dimethyl-phenoxy)-phenyl]-morpholine (0.60 g; 1.9 mmol), tert-butyl methacrylate (0.61 ml; 3.8 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.84 ml; 5.6 mmol), and DMF (10 mL) was heated at 140° C., overnight, in a closed vessel. After cooling to room temperature, the mixture was partitioned between 5% aqueous NaHCO3 and EtOAc. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O/hexanes 1:9) to afford 3-{2-[4-(2,3-dimethyl-phenoxy)-phenyl]-morpholin-4-yl}-2-methyl-propionic acid tert-butyl ester (0.27 g).

Workup

temperatureAfter cooling to room temperature
customthe mixture was partitioned between 5% aqueous NaHCO3 and EtOAc
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (SiO2, Et2O/hexanes 1:9)

Sources & evidence

ORD record: ord-1af66178a53648db9804f69a37d30fd1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227960B2

Reaction notes

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