Chlorotrimethylsilane → Benzyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 2168670Notes

Reaction equation

HRID 2168670 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[CH3:18][Si:19](Cl)([CH3:21])[CH3:20]>CN(C=O)C>[CH2:11]([O:10][C:8]([N:5]1[CH2:4][CH:3]=[C:2]([O:1][Si:19]([CH3:21])([CH3:20])[CH3:18])[CH2:7][CH2:6]1)=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 643496Benzyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 57502431Benzyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylateYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of benzyl 4-oxopiperidine-1-carboxylate (4.0 g, 17.2 mmol) in DMF (20 mL) was added TEA (9.0 mL) and TMSCl (4.0 mL, 32 mmol). The mixture was stirred overnight at 80° C., cooled, diluted with hexanes and washed with water. The organics were dried over sodium sulfate, filtered, concentrated, and purified by column chromatography using 10% EtOAc in hexanes to give 4-trimethylsilanyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester (5 g).

Workup

  1. temperaturecooled
  2. washwashed with water
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-8b6a129d0a744b528392c48f61e71435
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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