Propargyl alcohol → HCID 178463301, compound

HRID 1469158Notes

Reaction equation

HRID 1469158 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH3:23])[CH2:18][CH2:17]2)[CH2:14][CH3:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(NC(C)C)(C)C.[CH2:38]([OH:41])[C:39]#[CH:40]>C1(C)C=CC=CC=1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:27]([O:26][C:24]([N:22]([CH3:23])[C@H:19]1[CH2:20][CH2:21][C@H:16]([N:13]([CH2:14][CH3:15])[C:4]2[C:5]([CH3:12])=[C:6]([CH:11]=[C:2]([C:40]#[C:39][CH2:38][OH:41])[CH:3]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:17][CH2:18]1)=[O:25])([CH3:28])([CH3:29])[CH3:30]

Participants

8

Reactant 3

HCID 7859Propargyl alcoholHCID 7912DiisopropylamineHCID 178463214HCID 178463214, compound

Product 1

HCID 178463301HCID 178463301, compoundYield 63.2%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)(methyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate (2 g, 4.14 mmol) in dry toluene was added CuI (0.015 g, 0.079 mmol), PPh3 (0.043 g, 0.165 mmol), PdCl2(PPh3)2 (0.058 g, 0.082 mmol), N,N-diisopropyl amine (1.08 g, 10.78 mmol) and reaction was purged with argon for 15 min. prop-2-yn-1-ol (0.46 g, 8.29 mmol) was added to it reaction was heated at 80° C. at sealed condition for 5 h. On completion, it was quenched with water and extracted with ethyl acetate. Organic layer was dried over Na2SO4. The crude compound was purified by column chromatography to afford the title compound (1.2 g, 63.2% yield).

Workup

  1. additionwas added to it reaction
  2. customat sealed condition for 5 h
  3. customOn completion, it was quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialOrganic layer was dried over Na2SO4
  6. customThe crude compound was purified by column chromatography

Sources & evidence

ORD record
ord-f9d00b1007a84423b0fdc450db2300a1
Source dataset
uspto-grants-2015_04
Patent number
US09006242B2

Reaction notes

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