Triphenylphosphine → 1-(3-Methyl-1,2,4-oxadiazol-5-yl)-4-({[4'-(methylsulfonyl)-4-biphenylyl]oxy}methyl)piperidine

HRID 423479

Reaction equation

HRID 423479 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:18][C:19]1[N:23]=[C:22]([N:24]2[CH2:29][CH2:28][CH:27]([CH2:30]O)[CH2:26][CH2:25]2)[O:21][N:20]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:18][C:19]1[N:23]=[C:22]([N:24]2[CH2:25][CH2:26][CH:27]([CH2:30][O:17][C:14]3[CH:15]=[CH:16][C:11]([C:8]4[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=4)=[CH:12][CH:13]=3)[CH2:28][CH2:29]2)[O:21][N:20]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 149826764'-(Methylsulfonyl)-[1,1'-biphenyl]-4-olHCID 59177773[1-(3-Methyl-1,2,4-oxadiazol-5-yl)-4-piperidinyl]methanol

Product 1

HCID 591777711-(3-Methyl-1,2,4-oxadiazol-5-yl)-4-({[4'-(methylsulfonyl)-4-biphenylyl]oxy}methyl)piperidineYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound (43 mg, 21%) was prepared as a white solid from 4′-(methylsulfonyl)-4-biphenylol (prepared as in Example 1, Step 1, 120 mg, 0.48 mmol), [1-(3-methyl-1,2,4-oxadiazol-5-yl)-4-piperidinyl]methanol (143 mg, 0.73 mmol) and Ph3P (191 mg, 0.73 mmol) in THF (5 mL) followed by diisopropyl azodicarboxylate (0.144 mL, 0.73 mmol) in a manner similar to Example 1, Step 2, and worked up in a manner similar to Example 9, Step 3. 1H NMR (400 MHz, CDCl3): δ 7.97 (d, 2H, J=8.6 Hz), 7.72 (d, 2H, J=8.4 Hz), 7.55 (d, 2H, J=8.8 Hz), 6.99 (d, 2H, J=8.8 Hz), 4.25-4.15 (m, 2H), 3.89 (d, 2H, J=6.4 Hz), 3.22-3.08 (m, 2H), 3.08 (s, 3 H), 2.24 (s, 3H), 2.04-1.94 (m, 2H), 1.55-1.42 (m, 3H); LRMS (ESI), m/z 428 (M+H).

Sources & evidence

ORD record
ord-561c2a88d7354309b509cab9718af948
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Linked notes

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