Sodium Hydroxide → 1,1-Dimethylethyl 4-[({4-[5-(methylsulfonyl)-2-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylate

HRID 423524Notes

Reaction equation

HRID 423524 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[Na+].[CH3:30][S:31]([O-:33])=[O:32].N1CCC[C@H]1C(O)=O.[OH-].[Na+]>CS(C)=O>[CH3:30][S:31]([C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)=[CH:10][CH:9]=2)=[N:6][CH:7]=1)(=[O:33])=[O:32]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 2733271Sodium methanesulfinateHCID 666732311,1-Dimethylethyl 4-({[4-(5-bromo-2-pyridinyl)phenyl]oxy}methyl)-1-piperidinecarboxylate

Product 1

HCID 249943371,1-Dimethylethyl 4-[({4-[5-(methylsulfonyl)-2-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound (0.20 g, 80%) was prepared as a white solid from 1,1-dimethylethyl 4-({[4-(5-bromo-2-pyridinyl)phenyl]oxy}methyl)-1-piperidinecarboxylate (0.25 g, 0.60 mmol), methanesulfinic acid sodium salt (0.12 g, 80%, 0.91 mmol), L-proline (14 mg, 0.12 mmol), Cul (12 mg, 0.06 mmol) and NaOH (5 mg, 0.12 mmol) in DMSO (3 mL) in a manner similar to Example 76, Step 3. 1H NMR (400 MHz, CD3OD): δ 9.05 (d, 1H, J=2.2 Hz), 8.30 (dd, 1H, Ja=8.4 Hz, Jb=2.3 Hz), 8.09 (d, 2H, J=8.8 Hz), 8.04 (d, 1H, J=8.5 Hz), 7.06 (d, 2H, J=8.8 Hz), 4.20-4.10 (m, 2H), 3.93 (d, 2H, J=6.4 Hz), 3.21 (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 (m, 2H); LRMS (ESI), m/z 447 (M+H).

Sources & evidence

ORD record
ord-3c0a328cdfc3453b9e00f370ee892746
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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