Toluene → HCID 178469208, compound

HRID 525474Notes

Reaction equation

HRID 525474 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([OH:23])[CH:19]=3)[CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:24][C:25]([C@H:29]1[CH2:34][CH2:33][C@H:32](O)[CH2:31][CH2:30]1)([CH3:28])[CH2:26][CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[C:25]([C@@H:29]1[CH2:30][CH2:31][C@H:32]([O:23][C:18]2[CH:19]=[C:20]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([CH2:12][N:9]2[CH2:10][CH2:11][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8]2)[CH:22]=[CH:21]3)[CH2:33][CH2:34]1)([CH2:26][CH3:27])([CH3:24])[CH3:28]

Participants

6

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68279222Ethyl 1-((6-hydroxynaphthalen-2-yl)methyl)piperidine-4-carboxylateHCID 178444571HCID 178444571, compound

Product 1

HCID 178469208HCID 178469208, compoundYield 100.7%

Procedure

A mixture of 1-(6-hydroxy-naphthalen-2-ylmethyl)-piperidine-4-carboxylic acid ethyl ester (0.400 g, 1.28 mmol), trans-4-(1,1-dimethyl-propyl)-cyclohexanol (0.2395 g, 1.406 mmol) and triphenylphosphine (0.6695 g, 2.553 mmol) in toluene (5 mL, 40 mmol) was stirred for 20 min, then, diisopropyl azodicarboxylate (0.32 mL, 1.5 mmol) was added drop wise at 0° C. The solution was stirred at reflux overnight. The reaction was added to silica gel and the solvent was concentrated. The residue was purified with silica gel eluted with EtOAc in hexanes from 0 to 20% to give product as oil (0.6 g, 100%). LCMS: Rt=1.95 min, m/z=466.49 [M+H].

Workup

  1. stirringThe solution was stirred
  2. temperatureat reflux overnight
  3. additionThe reaction was added to silica gel
  4. concentrationthe solvent was concentrated
  5. customThe residue was purified with silica gel
  6. washeluted with EtOAc in hexanes from 0 to 20%

Sources & evidence

ORD record
ord-93751a7d073343f5897f8bc5c9556647
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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