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

HRID 1887547Notes

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

Workup

temperatureThe reaction mixture was then heated
temperatureunder reflux for 6 h
extractionThe aqueous phase was extracted three times with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulfate
customthe solvent was removed in vacuo
customThe crude product was purified by preparative HPLC
customThe product with the molecular weight of 173.12 (C12H15N) was obtained in this way

Sources & evidence

ORD record: ord-2cd5d6a3dc1540cc80221d7e815ef1be
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501771B2

Reaction notes

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