8-Methoxy-2,3,4,5,6,7-hexahydroazocine → 3-Trityl-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine

HRID 349170Notes

Reaction equation

HRID 349170 reaction equation
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([NH:10][NH2:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[C:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][N:33]=1>C1(C)C=CC=CC=1>[C:7]([C:8]1[N:33]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][C:26]2=[N:11][N:10]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 122610598-Methoxy-2,3,4,5,6,7-hexahydroazocineHCID 153699862,2,2-Triphenylacetohydrazide

Product 1

HCID 100235123-Trityl-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocineYield 19.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,2,2-Triphenylacetohydrazide (48.2 mg, 0.159 mmol) was dissolved in anhydrous toluene (3 mL) and stirred at room temperature under nitrogen. 8-Methoxy-2,3,4,5,6,7-hexahydroazocine (24.7 mg, 0.175 mmole) was added and the solution was stirred at 120° C. overnight and 200° C. for two days. After cooling, the toluene was removed by evaporation and crude product was purified by silica gel chromatography (100% ethyl acetate→5% methanol in ethyl acetate→10% methanol in ethyl acetate) to give the product (2-1) as a white solid (12.4 mg).

Workup

  1. stirringthe solution was stirred at 120° C. overnight and 200° C. for two days
  2. temperatureAfter cooling
  3. customthe toluene was removed by evaporation and crude product
  4. customwas purified by silica gel chromatography (100% ethyl acetate→5% methanol in ethyl acetate→10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-26afdce127264b718a6f7707cef3212e
Source dataset
uspto-grants-2007_02
Patent number
US07179802B2

Reaction notes

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