Sodium Iodide → 3-[2-(4-Octyloxy-phenyl)-morpholin-4-yl]-butyric acid tert-butyl ester

HRID 920584Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-(4-octyloxy-phenyl)-morpholine (0.24 gram, 1.1 mmol), 3-bromobutyric acid tert-butyl ester (0.24 g; 1.1 mmol), sodium iodide (27.4 mg; 0.2 mmol), and DBU (0.4 mL; 2.7 mmol) in CH3CN (10 mL) was heated in a closed vessel at 120° C. 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) to afford 3-[2-(4-octyloxy-phenyl)-morpholin-4-yl]-butyric acid tert-butyl ester (0.15 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)

Sources & evidence

ORD record: ord-90581374fad244ec972668292d2ee387
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273017B2

Reaction notes

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