Di-tert-butyl dicarbonate → tert-Butyl 3-[(2-methyl-2-propen-1-yl)oxy]-4-oxopiperidine-1-carboxylate

HRID 1425153Notes

Reaction equation

HRID 1425153 reaction equation
C[O:2][C:3]1(OC)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH:4]1[O:16][CH2:17][C:18]([CH3:20])=[CH2:19].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>O.C(O)(C(F)(F)F)=O>[CH3:20][C:18](=[CH2:19])[CH2:17][O:16][CH:4]1[C:3](=[O:2])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5]1

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 86712356tert-Butyl 4,4-dimethoxy-3-[(2-methyl-2-propen-1-yl)oxy]piperidine-1-carboxylate

Product 1

HCID 67549026tert-Butyl 3-[(2-methyl-2-propen-1-yl)oxy]-4-oxopiperidine-1-carboxylateYield 68.1%

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

The same operation as in Example (90b) was performed using tert-butyl 4,4-dimethoxy-3-[(2-methyl-2-propen-1-yl)oxy]piperidine-1-carboxylate obtained in Example (117a) (4.8 g, 18.7 mmol), a water/TFA mixed solution (1/1, 20 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 3.43 g of the title compound as a light brown oily substance (84%).

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-5bd297128d684ca5ac414096f6e66c80
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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