Triphenylphosphine → HCID 24993711, compound

HRID 423496Notes

Reaction equation

HRID 423496 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[C:19]([N:26]1[CH2:31][CH2:30][CH:29]([CH2:32]O)[CH2:28][CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].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>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:32][CH:29]1[CH2:30][CH2:31][N:26]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 532196743-Fluoro-4'-(methanesulfonyl)[1,1'-biphenyl]-4-ol

Product 1

HCID 24993711HCID 24993711, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound (0.32 g, 88%) was prepared as a white solid from 3-fluoro-4′-(methylsulfonyl)-4-biphenylol (0.21 g, 0.79 mmol), N-Boc-4-piperidinemethanol (0.18 g, 0.79 mmol) and Ph3P (0.21 g, 0.79 mmol) in THF (5 mL) followed by diisopropyl azodicarboxylate (0.17 g, 94%, 0.79 mmol) in THF (1.5 mL) in a manner similar to Example 1, Step 2. 1H NMR (400 MHz, CDCl3): δ 7.98 (d, 2H, J=8.6 Hz), 7.70 (d, 2H, J=8.6 Hz), 7.40-7.30 (m, 2H), 7.06 (t, 1H, J=8.5 Hz), 4.25-4.15 (m, 2H), 3.92 (d, 2H, J=6.3 Hz), 3.08 (s, 3H), 2.80-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.46 (s, 9H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 464 (M+H).

Sources & evidence

ORD record
ord-2d67589432a647f2b635b8d280eef3d6
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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