Pyridine → HCID 12709388, compound

HRID 1265939Notes

Reaction equation

HRID 1265939 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5](O)[CH2:4][C:3]1([CH3:12])[CH3:11].N(O[C:16]([CH3:19])([CH3:18])[CH3:17])=O.CC([O:24]NC1C=CC=CC=1)C=C.N1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[O:24]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:18]=2[CH:16]([CH2:19][O:1][N:2]2[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]2([CH3:12])[CH3:11])[CH2:17]1

Participants

5

Reactant 4

HCID 1049Pyridine2×HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 10906Tert-Butyl nitriteHCID 12032614HCID 12032614, compound

Product 1

HCID 12709388HCID 12709388, compoundYield 92.4%

Procedure

The procedure of Example 1 is repeated using 3.0 g (19 mmol) of 1-oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidine, 4.64 g (45 mmol) of tert-butyl nitrite, 11.45 mg (0.019 mmol) of (S,S)-(+)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) mmol) in 80 mL of pyridine and 6.27 g (38 mmol) of 2-(1-methylallyloxyaniline in 10 mL of pyridine. The crude product obtained is purified by vacuum flash chromatography (25% ethyl acetate/heptane) to give 5.31 g of a viscous liquid in 92.4% yield. The cis and trans isomers can be further separated by chromatography. The structures are confirmed by 1Hnmr analysis.

Workup

  1. customThe crude product obtained
  2. customis purified by vacuum flash chromatography (25% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-01d3993abe7743659cf08847fc301361
Source dataset
uspto-grants-2003_04
Patent number
US06547841B2

Reaction notes

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