Triphenylphosphine → 1,1-Dimethylethyl 4-({[2'-fluoro-4'-(methylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylate

HRID 423498Notes

Reaction equation

HRID 423498 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=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]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][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:14][CH:13]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 666730152'-Fluoro-4'-(methylsulfonyl)-4-biphenylol

Product 1

HCID 249937121,1-Dimethylethyl 4-({[2'-fluoro-4'-(methylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound (0.51 g, 85%) was prepared as a white solid from 2′-fluoro-4′-(methylsulfonyl)-4-biphenylol (0.34 g, 1.28 mmol), N-Boc-4-piperidinemethanol (0.29 g, 1.28 mmol) and Ph3P (0.34 g, 1.28 mmol) in THF (8 mL) followed by diisopropyl azodicarboxylate (0.28 g, 94%, 1.28 mmol) in THF (2.5 mL) in a manner similar to Example 1, Step 2. 1H NMR (400 MHz, CD3OD): δ 7.85-7.70 (m, 3H), 7.54 (d, 2H, J=7.3 Hz), 7.04 (d, 2H, J=8.8 Hz), 4.15-4.05 (m, 2H), 3.90 (d, 2H, J=6.1 Hz), 3.16 (s, 3H), 2.90-2.75 (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-de5d7f3106da4451ab82732350d47cdb
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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