4-Nitrophenol → (2-Isopropoxy-5-methanesulfonyl-phenyl)-[4-(4-nitro-phenoxy)-piperidin-1-yl]-methanone

HRID 1711736Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:15]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:13]=[CH:12][C:11]=2[O:20][CH:21]([CH3:23])[CH3:22])=[O:9])[CH2:4][CH2:3]1.[N+:24]([C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1)([O-:26])=[O:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[CH:21]([O:20][C:11]1[CH:12]=[CH:13][C:14]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:15][C:10]=1[C:8]([N:5]1[CH2:4][CH2:3][CH:2]([O:1][C:30]2[CH:31]=[CH:32][C:27]([N+:24]([O-:26])=[O:25])=[CH:28][CH:29]=2)[CH2:7][CH2:6]1)=[O:9])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 0.15 mmol (4-hydroxy-piperidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone (Example 3(a)) in 3 ml tetrahydrofuran were added successively 0.18 mmol 4-nitrophenol, 0.18 mmol triphenylphosphine and 0.18 mmol di-tert-butyl azodicarboxylate. The reaction mixture was stirred at 50° C. for 16 h and was then cooled to room temperature and concentrated in vacuo. The crude material was purified by reversed phase HPLC (acetonitrile/water) to afford the title compound as a white crystalline solid (yield 27%). MS (m/e): 463.4 (M+H+, 100%).

Workup

temperaturewas then cooled to room temperature
concentrationconcentrated in vacuo
customThe crude material was purified by reversed phase HPLC (acetonitrile/water)

Sources & evidence

ORD record: ord-7f05a96921014898a8f2143c1dcea9bf
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790763B2

Reaction notes

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