Di-tert-butyl dicarbonate → tert-Butyl 3-[(2E)-2-buten-1-yloxy]-4-oxopiperidine-1-carboxylate

HRID 43683Notes

Reaction equation

HRID 43683 reaction equation
[CH2:1]([O:5][CH:6]1[C:11](OC)([O:12]C)[CH2:10][CH2:9][N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7]1)/[CH:2]=[CH:3]/[CH3:4].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>O.C(O)(C(F)(F)F)=O>[CH2:1]([O:5][CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:7]1)/[CH:2]=[CH:3]/[CH3:4]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 67549820tert-Butyl 3-[(2E)-2-buten-1-yloxy]-4,4-dimethoxypiperidine-1-carboxylate

Product 1

HCID 67548695tert-Butyl 3-[(2E)-2-buten-1-yloxy]-4-oxopiperidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

The same operation as in Example (90b) was performed using tert-butyl 3-[(2E)-2-buten-1-yloxy]-4,4-dimethoxypiperidine-1-carboxylate obtained in Example (119a) (5.05 g, 16.0 mmol), a water/TFA mixed solution (1/1, 20 mL) and di-tert-butyl dicarbonate (5.2 g, 23.8 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 4.31 g of the title compound as a light brown oily substance (100%).

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-643cf5136d3f432aaf17b64a38ba4239
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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