Isobutylene oxide → 1-(4-((6-Chloropyridin-3-yl)oxy)piperidin-1-yl)-2-methylpropan-2-ol

HRID 1467996Notes

Reaction equation

HRID 1467996 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15](OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH3:22][C:23]1(C)[CH2:25][O:24]1>ClCCl.FC(F)(F)C(O)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:23]([CH3:25])([OH:24])[CH3:22])[CH2:13][CH2:14]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11208Isobutylene oxideHCID 86696180Tert-butyl 4-((6-chloropyridin-3-yl)oxy)piperidine-1-carboxylate

Product 1

HCID 866961911-(4-((6-Chloropyridin-3-yl)oxy)piperidin-1-yl)-2-methylpropan-2-olYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of tert-butyl 4-((6-chloropyridin-3-yl)oxy)piperidine-1-carboxylate (1.0 g, 3.2 mmol) in dichloromethane (10 mL), trifluoroacetic acid (3 mL) was added at 0° C. and stirred for 3 h. The reaction mixture was concentrated in vacuo and resultant residue was dissolved in MeOH (5 mL), 2,2-dimethyloxirane (0.246 g, 3.2 mmol) was added and stirred at room temperature for 10-12 h. The reaction mixture was concentrated in vacuo to give the title product (0.775, 85%); MS: 285.0 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and resultant residue
  2. dissolutionwas dissolved in MeOH (5 mL)
  3. stirringstirred at room temperature for 10-12 h
  4. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-b306180a5f514d55b73bbebd4f6a43ab
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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