Water → tert-Butyl 3-methoxy-4-oxopiperidine-1-carboxylate

HRID 2168195Notes

Reaction equation

HRID 2168195 reaction equation
[CH3:1][O:2][CH:3]1[C:8](OC)([O:9]C)[CH2:7][CH2:6][N:5]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:4]1.O.[OH-].[Na+].CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>Cl.O1CCOCC1>[CH3:1][O:2][CH:3]1[C:8](=[O:9])[CH2:7][CH2:6][N:5]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 592630891-Boc-3,4,4-trimethoxypiperidine

Product 1

HCID 57363786tert-Butyl 3-methoxy-4-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

To a solution of 1,1-dimethylethyl 3,4,4-tris(methyloxy)-1-piperidinecarboxylate D17 (4.85 g) in HCl/1,4-Dioxane (50 mL) was heated at 50° C. and stirred overnight. Water (50 ml) was added to the reaction mixture and the pH adjusted to 10.0 using sodium hydroxide. After that BOC anhydride (4.22 g, 19.4 mmol) was added to the reaction mixture and stirred for 4 hours. The resulting mixture was extracted with EtOAc (3×100 ml). The organic layer was dried over anhydrous MgSO4, concentrated in vacuo to afford the desired product D18 in 3.1 g. LCMS [M-55][email protected] min (5 min run)

Workup

  1. stirringstirred for 4 hours
  2. extractionThe resulting mixture was extracted with EtOAc (3×100 ml)
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-545840e34cca4f5fb63f3a87db2506a7
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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