Hydrochloric Acid → 3-Benzyl-3-azabicyclo[3.1.0]hexane

HRID 69466Notes

Reaction equation

II.[BH4-].[Na+].[CH2:5]([N:12]1[C:17](=O)[CH:16]2[CH:14]([CH2:15]2)[C:13]1=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[OH-].[Na+]>C1COCC1>[CH2:5]([N:12]1[CH2:13][CH:14]2[CH:16]([CH2:15]2)[CH2:17]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of iodine (2.27 g) in THF (27.9 mL) was added dropwise at 0° C. to a mixture of sodium borohydride (818 mg) in dry THF (45 mL) within 40 min. At this temperature, a solution of 3-benzyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione (750 mg) in THF (11.1 mL) was then added dropwise. Then the reaction mixture was heated for 6 h under reflux. The mixture was cooled to 0° C., and 3N HCl was carefully added. Then the reaction solution was neutralized with 2N sodium hydroxide solution. The aqueous phase was extracted three times with ethyl acetate. The organic phases were combined, dried over sodium sulfate and the solvent was removed in vacuum. The raw product was purified by preparative HPLC. In this way the product was obtained with molecular weight 173.12 (C12H15N); MS (ESI): 174 (M+H+).

Workup

temperatureThen the reaction mixture was heated for 6 h
temperatureunder reflux
extractionThe aqueous phase was extracted three times with ethyl acetate
dry with materialdried over sodium sulfate
customthe solvent was removed in vacuum
customThe raw product was purified by preparative HPLC
customIn this way the product was obtained with molecular weight 173.12 (C12H15N)

Sources & evidence

ORD record: ord-0844ddba708c483a90b1ca3d02ef31af
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822495B2

Reaction notes

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