Water → 6-(3-Nitrophenyl)-3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hexan-2-one

HRID 1826418Notes

Reaction equation

Br[CH2:2][CH:3]1[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=2)[CH:4]1[C:15]([O:17]CC)=O.C(=O)([O-])O.[Na+].[C:25]1([CH2:31][CH2:32][CH2:33][NH2:34])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C)C=O>[N+:12]([C:8]1[CH:7]=[C:6]([CH:5]2[CH:4]3[CH:3]2[CH2:2][N:34]([CH2:33][CH2:32][CH2:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:15]3=[O:17])[CH:11]=[CH:10][CH:9]=1)([O-:14])=[O:13]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of ethyl 2-(bromomethyl)-3-(3-nitrophenyl)cyclopropane carboxylate (Preparation 23, 60 mg, 0.18 mmol) in N,N-dimethylformamide (2 ml) was added sodium hydrogen carbonate (30 mg, 0.36 mmol) and 3-phenylpropylamine (30 mg, 31 μl, 0.22 mmol). The mixture was heated to 150° C. for 1 hour, then cooled to room temperature and stirred for 16 hours. Water (30 ml) was added and the mixture was extracted with diethyl ether (2×50 ml). The combined extracts were concentrated in vacuo and the residue was purified by silica (5 g) column chromatography eluting with dichloromethane then 4:1 dichloromethane:ethyl acetate. Product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless glassy solid (55 mg, 90%).

Workup

temperaturecooled to room temperature
extractionthe mixture was extracted with diethyl ether (2×50 ml)
concentrationThe combined extracts were concentrated in vacuo
customthe residue was purified by silica (5 g) column chromatography
washeluting with dichloromethane
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e6c75fc90fc24182bed9d92b94dc8b68
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049444B2

Reaction notes

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