Pyridine → HCID 71182970, compound

HRID 1891402Notes

Reaction equation

HRID 1891402 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13][N:14]=[N+]=[N-])[O:10][C:9]2=[O:17])[CH:5]=[CH:4][C:3]=1[N:18]1[CH2:22][CH:21]2[CH2:23][C:24]3([CH2:29][CH:20]2[CH2:19]1)[O:28][CH2:27][CH2:26][O:25]3.N1C=CC=CC=1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(OCC)(=O)C.[Pd]>[C:36]([NH:14][CH2:13][C@@H:11]1[O:10][C:9](=[O:17])[N:8]([C:6]2[CH:5]=[CH:4][C:3]([N:18]3[CH2:22][CH:21]4[CH2:23][C:24]5([CH2:29][CH:20]4[CH2:19]3)[O:28][CH2:27][CH2:26][O:25]5)=[C:2]([F:1])[CH:7]=2)[CH2:12]1)(=[O:38])[CH3:37]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 71182914HCID 71182914, compound

Product 1

HCID 71182970HCID 71182970, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10 g (24.8 mmol) of 2-[2-fluoro-4-[(5R)-5-(azidomethyl)-2-oxo-3-oxazolidinyl]phenyl]-hexahydro-1H-spiro[cyclopenta[c]pyrrol-5,2′-[1,3]dioxolane] prepared in the step 9 was dissolved in 100 ml of ethyl acetate, and 1 g of 10% palladium/active carbon, 4.01 ml (45.6 mmol) of pyridine and 3.5 ml (37.2 mmol) of acetic anhydride were added, and then, the mixture was stirred for 5 hours under hydrogen gas balloon. After the reaction was completed, the reaction mixture was filtered to remove solid and concentrated under reduced pressure. The concentrate was separated by column chromatography to obtain 5.30 g (51%) of the title compound, of which NMR data is as follows.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto remove solid
  3. concentrationconcentrated under reduced pressure
  4. customThe concentrate was separated by column chromatography

Sources & evidence

ORD record
ord-a8b4a172a6d94159a86a5e46f8da7824
Source dataset
uspto-grants-2013_08
Patent number
US08507540B2

Reaction notes

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