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

HRID 1971948Notes

Reaction equation

HRID 1971948 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-b5a23556332845e2ac8adcafdb57cd2d
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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