Pyridine → HCID 178472339, compound

HRID 452535Notes

Reaction equation

HRID 452535 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[C:13](N)=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].N1C=CC=CC=1.N([O-])=O.[Na+].[FH:29]>>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[C:13]([F:29])=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 1049PyridineHCID 14917Hydrofluoric AcidHCID 23668193Sodium NitriteHCID 178472340HCID 178472340, compound

Product 1

HCID 178472339HCID 178472339, compoundYield 44%

Procedure

To a solution of trans-4-(2-amino-pyridin-3-yl)-cyclohexanecarboxylic acid ethyl ester (0.25 g, 1.0 mmol) in 70% hydrogen fluoride in pyridine (2.4 ml, 92 mmol) was added solid sodium nitrite (0.076 g, 1.1 mmol) at 0-5° C. The cooling bath was removed after 30 minutes and the reaction mixture was stirred for 2 h at room temperature. The reaction mixture was partitioned between an ice-water mixture (50 ml) and tert-butyl methyl ether (50 ml). The organic layer was collected. The aqueous layer was extracted with one 100-ml portion of tert-butyl methyl ether. The combined organic layers were dried over anhydrous sodium sulfate and concentrated to dryness. Flash-chromatography with n-heptane/ethyl acetate as eluent gives the title compound (0.11 g, 44%) as light yellow oil. MS m/e: 252 ([M+H]+)

Workup

  1. customThe cooling bath was removed after 30 minutes
  2. customThe reaction mixture was partitioned between an ice-water mixture (50 ml) and tert-butyl methyl ether (50 ml)
  3. customThe organic layer was collected
  4. extractionThe aqueous layer was extracted with one 100-ml portion of tert-butyl methyl ether
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fa673f470d784aaa86d4febe3de14e7f
Source dataset
uspto-grants-2013_07
Patent number
US08492376B2

Reaction notes

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