Iodoethane → Tert-butyl 3-ethoxy-4,4-dimethoxypiperidine-1-carboxylate

HRID 43647Notes

Reaction equation

HRID 43647 reaction equation
[OH:1][CH:2]1[C:7]([O:10][CH3:11])([O:8][CH3:9])[CH2:6][CH2:5][N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3]1.[H-].[Na+].I[CH2:22][CH3:23]>CN(C=O)C>[CH2:22]([O:1][CH:2]1[C:7]([O:8][CH3:9])([O:10][CH3:11])[CH2:6][CH2:5][N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3]1)[CH3:23]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 11425480Tert-butyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate

Product 1

HCID 68406637Tert-butyl 3-ethoxy-4,4-dimethoxypiperidine-1-carboxylateYield 84.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The same operation as in Example (90a) was performed using tert-butyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate (5.2 g, 20 mmol), sodium hydride (55% content, 1.31 g, 30 mmol), 1-iodoethane (6.24 g, 40 mmol) and DMF (50 mL). The residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=10/1, 4/1, 2/1) to obtain 4.90 g of the title compound as a colorless oily substance (85%).

Workup

  1. customThe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=10/1, 4/1, 2/1)

Sources & evidence

ORD record
ord-e5f805dc61a941628c9e8d1c8ac51136
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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