Cyclobutanone → 1-(Cis-2-methyl-cyclohexyl)-pyrrolidin-2-one

HRID 2235203Notes

Reaction equation

[N:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:5]1[CH3:10])=[N+]=[N-].[C:11]1(=[O:15])[CH2:14][CH2:13][CH2:12]1>ClCCl.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-]>[CH3:10][C@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@H:4]1[N:1]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve cis-1-azido-2-methyl-cyclohexane (Preparation 31) (3.68 g, 26.41 mmol) and cyclobutanone (1.85 g, 26.41 mmol) in dichloromethane (200 mL). Cool the solution to 0° C. and add titanium chloride (15.03 g, 79.23 mmol) under nitrogen. Stir the reaction for 24 hours at room temperature. Add water (200 mL), and extract the aqueous layer with dichloromethane (3×200 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 20-50% of EtOAc/Hexane) to give 1.74 g (36%) of the title compound as a colorless oil.

Workup

customthe reaction for 24 hours at room temperature
extractionAdd water (200 mL), and extract the aqueous layer with dichloromethane (3×200 mL)
dry with materialCombine the organic layers and dry with Na2SO4
filtrationfilter
concentrationconcentrate
custompurify by flash column chromatography (silica gel, 20-50% of EtOAc/Hexane)

Sources & evidence

ORD record: ord-7926f1bffe70403085aeb3fcdc2f5b96
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713979B2

Reaction notes

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