Cesium carbonate → 3-Neopentyl-7-(((2-nitro-5-(trifluoromethyl)phenyl)amino)methyl)-1-oxa-3-azaspiro[4.5]decan-2-one

HRID 1423844

Reaction equation

[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].Br[CH2:16][CH:17]1[CH2:32][CH2:31][CH2:30][C:19]2([O:23][C:22](=[O:24])[N:21]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:20]2)[CH2:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>CN(C=O)C>[CH2:25]([N:21]1[CH2:20][C:19]2([CH2:30][CH2:31][CH2:32][CH:17]([CH2:16][NH:6][C:5]3[CH:7]=[C:8]([C:11]([F:12])([F:13])[F:14])[CH:9]=[CH:10][C:4]=3[N+:1]([O-:3])=[O:2])[CH2:18]2)[O:23][C:22]1=[O:24])[C:26]([CH3:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution containing 2-nitro-5-(trifluoromethyl)aniline (0.777 g, 3.77 mmol) and 7-(bromomethyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one (1.00 g, 3.14 mmol) in DMF (15 mL) was treated with cesium carbonate (3.07 g, 9.43 mmol) and stirred at 60° C. overnight. The cooled reaction mixture was diluted with saturated, aqueous ammonium chloride solution, and the product was extracted into DCM. The organics were washed with brine, dried over Na2SO4, and concentrated. The residue was purified on a 120 g silica gel column (10-60 EtOAc/hexanes; 65 mL/min elution; 254 nm detection) to afford the title compound (0.260 g, 19 yield). MS (m/z) 444.2 (M+H+).

Workup

customThe cooled reaction mixture
extractionthe product was extracted into DCM
washThe organics were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified on a 120 g silica gel column (10-60 EtOAc/hexanes; 65 mL/min elution; 254 nm detection)

Sources & evidence

ORD record: ord-b430131e6fab47568898c5403af08fa0
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927585B2

Linked notes

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