Toluene → 1-[6-(Bicyclo[2.2.1]hept-5-en-2-yloxy)-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid ethyl ester

HRID 525494Notes

Reaction equation

HRID 525494 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:22][C:23]([CH:25]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[C:37]([OH:42])[CH:38]=3)[CH:33]=2)[CH2:27][CH2:26]1)=[O:24])[CH3:21].[CH:43]12[CH2:49][CH:46]([CH:47]=[CH:48]1)[CH2:45][CH:44]2O.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(OC(=O)C)C>[CH2:20]([O:22][C:23]([CH:25]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[C:37]([O:42][CH:48]4[CH2:47][CH:46]5[CH2:49][CH:43]4[CH:44]=[CH:45]5)[CH:38]=3)[CH:33]=2)[CH2:27][CH2:26]1)=[O:24])[CH3:21]

Participants

7

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 96066Bicyclo(2.2.1)hept-5-en-2-olHCID 68279222Ethyl 1-((6-hydroxynaphthalen-2-yl)methyl)piperidine-4-carboxylate

Product 1

HCID 682797911-[6-(Bicyclo[2.2.1]hept-5-en-2-yloxy)-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid ethyl esterYield 8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triphenylphosphine was added to a solution of 1-(6-Hydroxy-naphthalen-2-ylmethyl)-piperidine-4-carboxylic acid ethyl ester (0.4319 g, 0.001378 mol) and bicyclo[2.2.1]hept-5-en-2-ol (0.243 g, 0.00220 mol) in toluene (0.881 mL, 0.00827 mol) and the mixture was stirred for several minutes. Diisopropyl azodicarboxylate (0.434 mL, 0.00220 mol) was then added dropwise and the mixture was stirred at room temperature for 72 hours. The reaction mixture was then diluted in ethylacetate and washed with water, then brine. The organic phase was dried over MgSO4, filtered, concentrated under reduced pressure and purified by flash chromatography (0-40% EtOAc in heptanes) to give the title compound in 8% yield. ESI-MS (M+H+): 406.2.

Workup

  1. stirringthe mixture was stirred at room temperature for 72 hours
  2. washwashed with water
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified by flash chromatography (0-40% EtOAc in heptanes)

Sources & evidence

ORD record
ord-a6b8faf40a81471c89381727a6660284
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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