Di-tert-butyl dicarbonate → Tert-butyl 3-ethoxy-4-oxopiperidine-1-carboxylate

HRID 43648Notes

Reaction equation

HRID 43648 reaction equation
[CH2:1]([O:3][CH:4]1[C:9](OC)([O:10]C)[CH2:8][CH2:7][N:6]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5]1)[CH3:2].O.C(O)(C(F)(F)F)=O.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>>[CH2:1]([O:3][CH:4]1[C:9](=[O:10])[CH2:8][CH2:7][N:6]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:5]1)[CH3:2]

Participants

4

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 22392675Trifluoroacetic acid waterHCID 68406637Tert-butyl 3-ethoxy-4,4-dimethoxypiperidine-1-carboxylate

Product 1

HCID 68406177Tert-butyl 3-ethoxy-4-oxopiperidine-1-carboxylateYield 95.5%

Procedure

The same operation as in Example (90b) was performed using tert-butyl 3-ethoxy-4,4-dimethoxypiperidine-1-carboxylate obtained in Example (112a) (4.99 g, 14.2 mmol), a water/TFA mixed solution (1/1, 35 mL) and di-tert-butyl dicarbonate (4.37 g, 20 mol). The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=10/1, 5/1, 2/1, 1/1) to obtain 3.3 g of the title compound as a light brown oily substance (77%).

Workup

  1. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=10/1, 5/1, 2/1, 1/1)

Sources & evidence

ORD record
ord-db4db5c93845483ab2bd2f99b586a6ad
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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