Di-tert-butyl dicarbonate → tert-Butyl 3-(2-fluoroethoxy)-4-oxopiperidine-1-carboxylate

HRID 43697Notes

Reaction equation

HRID 43697 reaction equation
[F:1][CH2:2][CH2:3][O:4][CH:5]1[C:10](OC)([O:11]C)[CH2:9][CH2:8][N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6]1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>O.C(O)(C(F)(F)F)=O>[F:1][CH2:2][CH2:3][O:4][CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6]1

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 86648640tert-Butyl 3-(2-fluoroethoxy)-4,4-dimethoxypiperidine-1-carboxylate

Product 1

HCID 86648641tert-Butyl 3-(2-fluoroethoxy)-4-oxopiperidine-1-carboxylateYield 97.5%

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

The same operation as in Example (90b) was performed using tert-butyl 3-(2-fluoroethoxy)-4,4-dimethoxypiperidine-1-carboxylate obtained in Example (123a) (6.5 g, 21.2 mmol), a water/TFA mixed solution (1/1, 20 mL) and di-tert-butyl dicarbonate (6.54 g, 30 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 5.4 g of the title compound as a light brown oily substance (98%).

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-9e4ac9b4776541ccb5a2e2315121d863
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

Loading…