Water → 3-Hexyl-6-phenyl-3-azabicyclo[3.1.0]hexan-2-one

HRID 428916Notes

Reaction equation

Br[CH2:2][CH:3]1[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:4]1[C:12]([O:14]CC)=O.C(=O)([O-])O.[Na+].[CH2:22]([NH2:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].O>CN(C)C=O>[CH2:22]([N:28]1[CH2:2][CH:3]2[CH:4]([CH:5]2[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:12]1=[O:14])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of ethyl 2-(bromomethyl)-3-phenylcyclopropanecarboxylate (Preparation 26, 65 mg, 0.22 mmol) in N,N-dimethylformamide (2 ml) was added sodium hydrogen carbonate (30 mg, 0.36 mmol) and hexylamine (33 μl, 26 mg, 0.26 mmol), and the mixture was heated to 150° C. for 3 h. The mixture was cooled, water (30 ml) was added, and the mixture was extracted with diethyl ether (2×30 ml). The extracts were combined, dried (Na2SO4), filtered and concentrated in vacuo. The mixture was purified by silica column (5 g) chromatography eluting with 4:1 dichloromethane:ethyl acetate. Product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless oil (45 mg, 76%).

Workup

temperatureThe mixture was cooled
extractionthe mixture was extracted with diethyl ether (2×30 ml)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe mixture was purified by silica column (5 g) chromatography
washeluting with 4:1 dichloromethane
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-aa864f240ed84c999ff42112ac25a9c0
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313312B1

Reaction notes

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