Triphenylphosphine → HCID 24994032, compound

HRID 423505Notes

Reaction equation

HRID 423505 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=1.[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:7]=[C:6]([O:8][CH2:32][CH:29]2[CH2:30][CH2:31][N:26]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:27][CH2:28]2)[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 532196762-Fluoro-4'-(methanesulfonyl)[1,1'-biphenyl]-4-ol

Product 1

HCID 24994032HCID 24994032, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared as a white solid from 2-fluoro-4′-(methylsulfonyl)-4-biphenylol (0.25 g, 0.94 mmol), N-Boc-4-piperidinemethanol (0.21 g, 0.94 mmol) and Ph3P (0.25 g, 0.94 mmol) in THF (6 mL) followed by diisopropyl azodicarboxylate (0.20 g, 94%, 0.94 mmol) in THF (2 mL) in a manner similar to Example 1, Step 2. The crude product was triturated with hot hexane containing 1% of MeOH to give 20 mg of the title compound as a white solid. The filtrate was purified by chromatography on a silica gel column eluted with 3:4 EtOAc/hexane to give additional 0.34 g (overall 83%) of the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ 7.99 (d, 2H, J=8.3 Hz), 7.76 (d, 2H, J=7.4 Hz), 7.50-7.40 (m, 1H), 6.90-6.80 (m, 2H), 4.20-4.10 (m, 2H), 3.91 (d, 2H, J=6.4 Hz), 3.14 (s, 3H), 2.90-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.45 (s, 9H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 486 (M+Na).

Workup

  1. customThe crude product was triturated with hot hexane containing 1% of MeOH

Sources & evidence

ORD record
ord-a074c674248242fdb52460ed5912c627
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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