Azidobenzene → 1-Tert-butoxycarbonyl-4-(1-phenyl-1,2,3-triazol-4-yl)-1,2,3,6-tetrahydropyridine

HRID 727090Notes

Reaction equation

HRID 727090 reaction equation
[C:1]1([N:7]=[N+:8]=[N-:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH:21]=[C:20]([C:23]#[CH:24])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>C1(C)C=CC=CC=1>[C:10]([O:14][C:15]([N:17]1[CH2:18][CH:19]=[C:20]([C:23]2[N:9]=[N:8][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:24]=2)[CH2:21][CH2:22]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 69319AzidobenzeneHCID 18942198tert-Butyl 4-ethynyl-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 197052921-Tert-butoxycarbonyl-4-(1-phenyl-1,2,3-triazol-4-yl)-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the crude phenylazide (1.37 g, 11.5 mmol) from above and 1-tert-butoxycarbonyl-4-ethynyl-1,2,3,6-tetrahydropyridine (2 g, 9.6 mmol) (Example 1) in toluene (20 ml) was refluxed for 24 hours. The reaction was cooled and the solvent evaporated in vacuo. The crude residue was chromatographed on silica eluting with ethyl acetate/petrol (60°-80° C.) (1:2) to give the 1-tert-butoxycarbonyl-4-(1-phenyl-1,2,3-triazol-4-yl)-1,2,3,6-tetrahydropyridine as a tan waxy solid (853 mg, 27%), δH (CDCl3) 1.49 (9H, s, OC(CH3)3), 2.59 (2H, br s, tetrahydropyridinyl CH2), 3.67 (2H, t, J 5.2 Hz, tetrahydropyridinyl CH2), 4.12 (2H, br s, tetrahydropyridinyl CH2), 6.53 (1H, br s, tetrahydropyridinyl 5-H), 7.42-7.46 (1H, m, ArH), 7.51-7.55 (2H, m, ArH), 7.72-7.75 (2H, m, ArH), 7.87 (1H, s, triazolyl 5-H).

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperatureThe reaction was cooled
  3. customthe solvent evaporated in vacuo
  4. customThe crude residue was chromatographed on silica eluting with ethyl acetate/petrol (60°-80° C.) (1:2)

Sources & evidence

ORD record
ord-0dee9093aaaf472593d8efb6850124f3
Source dataset
uspto-grants-1998_01
Patent number
US05712285

Reaction notes

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