Ammonium formate → HCID 68749290, compound

HRID 1864778Notes

Reaction equation

HRID 1864778 reaction equation
[CH3:1][Si:2]([CH3:16])([CH3:15])[CH2:3][CH2:4][O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7].C([O-])=O.[NH4+:20]>[Pd].O.CO>[CH3:1][Si:2]([CH3:16])([CH3:15])[CH2:3][CH2:4][O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:20])[CH2:10][CH2:9]1)=[O:7]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 222659502-(Trimethylsilyl)ethyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 68749290HCID 68749290, compoundYield 40.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A slurry of 10% palladium on carbon (200 mg) in water was added to 4-oxo-piperidine-1-carboxylic acid-2-trimethylsilanyl-ethyl ester (2.42 g, 10 mmol) in 100 mL of methanol. Ammonium formate (6.0 g, 95 mmol) in water was added dropwise, and the mixture stirred vigorously overnight. The mixture was filtered and the filtrate concentrated in vacuo to leave the crude product. Chromatography (elution with methanol-dichloromethane) provided 0.98 g of product.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto leave the crude product
  4. washChromatography (elution with methanol-dichloromethane)

Sources & evidence

ORD record
ord-e09efe30857045cbbddb93b978dbd682
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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