Triphenylphosphine → 1,1-Dimethylethyl 4-[({4-[6-(methylsulfonyl)-3-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylate

HRID 423517Notes

Reaction equation

HRID 423517 reaction equation
[CH3:1][S:2]([C:5]1[N: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].[C:18]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31]O)[CH2:27][CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].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>[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:31][CH:28]3[CH2:29][CH2:30][N:25]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:26][CH2:27]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 574579804-(6-(Methylsulfonyl)pyridin-3-yl)phenol

Product 1

HCID 249943351,1-Dimethylethyl 4-[({4-[6-(methylsulfonyl)-3-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylateYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound (0.34 g, 75%) was prepared as a white solid from 4-[6-(methylsulfonyl)-3-pyridinyl]phenol (0.25 g, 1.00 mmol), N-Boc-4-piperidinemethanol (0.23 g, 1.00 mmol) and Ph3P (0.27 g, 1.00 mmol) in THF (6 mL) followed by diisopropyl azodicarboxylate (0.22 g, 94%, 1.0 mmol) in THF (2 mL) in a manner similar to Example 1, Step 2. 1H NMR (400 MHz, CD3OD): δ 8.96 (d, 1H, J=2.2 Hz), 8.28 (dd, 1H, Ja=8.3 Hz, Jb=2.2 Hz), 8.10 (d, 1H, J=8.1 Hz), 7.70 (d, 2H, 8.8 Hz), 7.08 (d, 2H, J=8.8 Hz), 4.20-4.10 (m, 2H), 3.92 (d, 2H, J=6.1 Hz), 3.24 (s, 3H), 2.90-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.46 (s, 9H), 1.35-1.20 (2H); LRMS (APCI), m/z 469 (M+Na).

Sources & evidence

ORD record
ord-6bcc72322b2a428884c7f398463d9874
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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