1-((4-Bromophenyl)diazenyl)pyrrolidine → 3-(4-(Pyrrolidin-1-yldiazenyl)phenyl)oxetan-3-ol

HRID 522666Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]=[N:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[Li]CCCC.[O:20]1[CH2:23][C:22](=[O:24])[CH2:21]1>C1COCC1>[N:10]1([N:9]=[N:8][C:5]2[CH:6]=[CH:7][C:2]([C:22]3([OH:24])[CH2:23][O:20][CH2:21]3)=[CH:3][CH:4]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 1-((4-bromophenyl)diazenyl)pyrrolidine (500 mg, 1.97 mmol) in anhydrous THF (20 mL) was added n-BuLi (1.8 mL, 4.33 mmol) dropwise at −78° C. under N2. The solution was stirred at −78° C. for 1 h, followed by the addition of oxetan-3-one (326 mg, 4.53 mmol). The resultant mixture was stirred at RT for 18 h. The reaction was quenched by saturated aqueous NH4Cl aq. (20 mL) and extracted with ethyl acetate (20 mL*3). The combined organic layers were concentrated under reduced pressure to give a residue, which was purified by silica gel chromatography (DCM:MeOH=20:1) to afford the title compound (500 mg, yield 97%) as a light yellow solid. MS (ES+) C13H17N3O2 requires: 247, found 248 [M+H]+, purity: 90%.

Workup

customThe reaction was quenched by saturated aqueous NH4Cl aq. (20 mL)
extractionextracted with ethyl acetate (20 mL*3)
concentrationThe combined organic layers were concentrated under reduced pressure
customto give a residue, which
customwas purified by silica gel chromatography (DCM:MeOH=20:1)

Sources & evidence

ORD record: ord-d382f485bfa34df4a1d4a9d4037958be
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334263B2

Reaction notes

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