3-(4-(Pyrrolidin-1-yldiazenyl)phenyl)oxetan-3-ol → 3-(4-Aminophenyl)oxetan-3-ol

HRID 522667Notes

Reaction equation

N1(N=[N:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3([OH:18])[CH2:17][O:16][CH2:15]3)=[CH:10][CH:9]=2)CCCC1>CO.[Pd]>[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2([OH:18])[CH2:15][O:16][CH2:17]2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 3-(4-(pyrrolidin-1-yldiazenyl)phenyl)oxetan-3-ol (500 mg, 2.02 mmol) in methanol (15 mL) was added Pd/C (10%, 250 mg) at RT. The reaction mixture was stirred under 1 atm H2 atmosphere (balloon) at 40° C. for 18 h. The mixture was filtered through a pad of Celite. The filtrate was concentrated to give a residue, which was purified by Prep-HPLC to afford the title compound (200 mg, yield 60%) as a white solid. MS (ES+) C9H11NO2 requires: 165, found 166 [M+H]+, purity: 96%.

Workup

filtrationThe mixture was filtered through a pad of Celite
concentrationThe filtrate was concentrated
customto give a residue, which
customwas purified by Prep-HPLC

Sources & evidence

ORD record: ord-d3af1d27ee514c4fab8b92baa4403be9
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334263B2

Reaction notes

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