Di-tert-butyl dicarbonate → tert-Butyl 3-allyloxy-4-oxopiperidine-1-carboxylate

HRID 43657Notes

Reaction equation

HRID 43657 reaction equation
[CH2:1]([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)[CH:2]=[CH2:3].O.C(O)(C(F)(F)F)=O.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>>[CH2:1]([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)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 22392675Trifluoroacetic acid waterHCID 68405955tert-Butyl 3-allyloxy-4,4-dimethoxypiperidine-1-carboxylate

Product 1

HCID 67548846tert-Butyl 3-allyloxy-4-oxopiperidine-1-carboxylateYield 91.5%

Procedure

The same operation as in Example (90b) was performed using tert-butyl 3-allyloxy-4,4-dimethoxypiperidine-1-carboxylate obtained in Example (113a) (5.64 g, 18.7 mmol), a water/TFA mixed solution (1/1, 35 mL) and di-tert-butyl dicarbonate (4.8 g, 22 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 4.37 g of the title compound as a light brown oily substance (91%).

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-e942eb1bc62241feb4bbf8a9ee5ddbca
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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