Hexylamine → 3-Hexyl-6-methyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexan-2-one

HRID 428905Notes

Reaction equation

Cl[CH2:2][CH:3]1[CH:5]([C:6]([O:8]CC)=O)[C:4]1([CH3:20])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1.[CH2:21]([NH2:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])O.[Na+]>O>[CH2:21]([N:27]1[CH2:2][CH:3]2[CH:5]([C:4]2([CH3:20])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:6]1=[O:8])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethyl 3-(chloromethyl)-2-methyl-2-(3-nitrophenyl)cyclopropane carboxylate (Preparation 5, 20 g, 67.2 mmol) in hexylamine (36 ml, 270 mmol) was added sodium hydrogen carbonate (5.64 g, 67.2 mmol), and the mixture was heated at 100° C. for 16 h. The rmixture was cooled, diluted with water (80 ml) and extracted with dichloromethane (3×150 ml). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica column chromatography, eluting with a gradient of 2:1 to 1:2 hexane/ethyl acetate. Appropriate fractions were combined and concentrated in vacuo to give the title compound as a very pale yellow oil (14.2 g, 67%).

Workup

temperatureThe rmixture was cooled
extractionextracted with dichloromethane (3×150 ml)
dry with materialThe combined extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica column chromatography
washeluting with a gradient of 2:1 to 1:2 hexane/ethyl acetate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2b23cb571cc542239f75b4a71f31a816
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313312B1

Reaction notes

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