Tetrabutylammonium Hydroxide → 5-Chloro-4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]oxypyridin-2-olate;tetrabutylazanium

HRID 1962277Notes

Reaction equation

HRID 1962277 reaction equation
[Cl:1][C:2]1[C:3]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[OH-].[CH2:24]([N+:28]([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH3:27]>N1C=CC=CC=1>[C:19]([O:18][C:16]([N:13]1[CH2:14][CH2:15][CH:10]([O:9][C:3]2[C:2]([Cl:1])=[CH:7][N:6]=[C:5]([O-:8])[CH:4]=2)[CH2:11][CH2:12]1)=[O:17])([CH3:22])([CH3:20])[CH3:21].[CH2:37]([N+:28]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:33][CH2:34][CH2:35][CH3:36])[CH2:38][CH2:39][CH3:40]

Participants

4

Reactant 2

HCID 2723671Tetrabutylammonium HydroxideHCID 58467944Tert-butyl 4-(5-chloro-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

Product 1

HCID 584679435-Chloro-4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]oxypyridin-2-olate;tetrabutylazanium

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A one liter round bottom flask was charged with t-butyl 4-(5-chloro-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate (69.2 g, 210 mmol) and pyridine (421 mL). The slurry was heated to 80° C. until all of the material dissolved to form a clear solution. At this temperature, tetrabutylammonium hydroxide solution (152 mL, 232 mmol) was added. The mixture was concentrated in vacuo and the residual water was azeotropically removed with toluene (3×300 ml). The residue was dried under high vacuum for 12 hours to give a wet solid which was used directly in the next reaction. 1H-NMR (CDCl3, 400 MHz) δ 7.65 (s, 1H), 5.83 (s, 1H), 4.40-4.60 (m, 1H), 3.55-3.75 (m, 2H), 3.20-3.46 (m, 10H), 1.72-2.0 (m, 4H); 1.55-1.72 (m, 8H), 1.30-1.55 (m, 17H), 1.0 (t, 12H, J=7.4 Hz); Anal. Calcd for C31H56ClN3O4.0.76H2O: C, 63.76; H, 9.93; N, 7.20; Cl, 6.07. Found: C, 63.76; H, 9.87; N, 7.09; Cl, 6.21.

Workup

  1. dissolutiondissolved
  2. customto form a clear solution
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residual water was azeotropically removed with toluene (3×300 ml)
  5. customThe residue was dried under high vacuum for 12 hours
  6. customto give a wet solid which
  7. customwas used directly in the next reaction

Sources & evidence

ORD record
ord-47f8fdbd0e594d4eada0fa78ff6a573d
Source dataset
uspto-grants-2013_04
Patent number
US08415367B2

Reaction notes

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