tert-Butyl methacrylate → HCID 67032358, compound

HRID 920583Notes

Reaction equation

Cl.[CH2:2]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[O:22][CH2:21][CH2:20][NH:19][CH2:18]2)=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:23]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[C:24]([CH3:26])=[CH2:25].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[C:29]([O:28][C:23](=[O:27])[CH:24]([CH3:26])[CH2:25][N:19]1[CH2:20][CH2:21][O:22][CH:17]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:16][CH:15]=2)[CH2:18]1)([CH3:32])([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 140 °C

Procedure

To a suspension of 2-(4-octyloxy-phenyl)-morpholine hydrochloride (0.17 g; 0.5 mmol) in DMF (5.00 mL) was added tert-butyl methacrylate (0.17 mL; 1.0 mmol) and DBU (0.23 mL; 1.5 mmol) The resulting mixture was heated at 140° C. in a sealed flask overnight. After cooling to RT the reaction mixture was partitioned between 5% aqueous NaHCO3 solution and EtOAc. The layers were separated and the organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (SiO2, Et2O:hexanes 1:1) to afford 2-methyl-3-[2-(4-octyloxy-phenyl)-morpholin-4-yl]-propionic acid tert-butyl ester (0.11 g).

Workup

temperatureAfter cooling to RT the reaction mixture
customwas partitioned between 5% aqueous NaHCO3 solution and EtOAc
customThe layers were separated
dry with materialthe organic layer was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography (SiO2, Et2O:hexanes 1:1)

Sources & evidence

ORD record: ord-eb34d2cae57d40ad8f752a9495072581
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273017B2

Reaction notes

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