Trimethylsilyldiazomethane → HCID 18670458, compound

HRID 1059321Notes

Reaction equation

HRID 1059321 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]([OH:26])=[O:25])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][Si](C=[N+]=[N-])(C)C>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 18670159HCID 18670159, compound

Product 1

HCID 18670458HCID 18670458, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.55 g of 4-[1-(benzyloxycarbonyl)-piperidin-4-yl]phenylacetic acid in methanol (20 ml) was added 13.2 ml of trimethylsilyldiazomethane (2 M solution in hexane) and the resulting mixture was reacted at room temperature for 1 hour. After distilling off the reaction mixture under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 1.0 of the title compound as a colorless oily substance.

Workup

  1. customthe resulting mixture was reacted at room temperature for 1 hour
  2. distillationAfter distilling off the reaction mixture under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-532c654d57394dff9fce55f508fce951
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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