Toluene → HCID 178422073, compound

HRID 713953Notes

Reaction equation

HRID 713953 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]1[N:22]=[CH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[C:26]([OH:31])[CH:25]=2.[C:32]([C@@H:36]1[CH2:41][CH2:40][C@H:39](O)[CH2:38][CH2:37]1)([CH3:35])([CH3:34])[CH3:33].C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[C:32]([C@H:36]1[CH2:41][CH2:40][C@H:39]([O:31][C:26]2[CH:25]=[C:24]3[C:29]([CH:30]=[C:21]([CH3:20])[N:22]=[CH:23]3)=[CH:28][CH:27]=2)[CH2:38][CH2:37]1)([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 123322583-Methylisoquinolin-7-olHCID 178445811HCID 178445811, compound

Product 1

HCID 178422073HCID 178422073, compoundYield 52%

Procedure

Triphenylphosphine (5.14 g, 19.6 mmol) was added to a solution of 3-Methyl-isoquinolin-7-ol (2.08 g, 13.1 mmol) and cis-4-tert-butylcyclohexanol (3.06 g, 19.6 mmol) in Toluene (60 mL, 600 mmol). The mixture was stirred for 15 minutes then Diisopropyl azodicarboxylate (3.86 mL, 19.6 mmol) was added. The mixture was then stirred at room temperature overnight. The solvent was removed under vacuum. The crude product was dissolved in methylene chloride, adsorbed onto silica gel and purified by flash chromatography (0-30% EtOAc in hexanes) to give the title compound in 52% yield. ESI-MS(M+H+): 298.46.

Workup

  1. stirringThe mixture was then stirred at room temperature overnight
  2. customThe solvent was removed under vacuum
  3. dissolutionThe crude product was dissolved in methylene chloride
  4. custompurified by flash chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b0322d8c1f144f1099f4c9b2bf197985
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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