Tetrahydrofuran → HCID 86760758, compound

HRID 271365Notes

Reaction equation

HRID 271365 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[NH:10][C@H:11]1[CH2:15][CH2:14][C@H:13]([O:16][CH2:17][C:18](Br)=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(O)(O)[C:29]1[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=1.[F-].[K+].O1CCCC1>C(=O)([O-])[O-].[Na+].[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(PC2CCCCC2)CCCCC1.C1(C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:27])[NH:10][C@H:11]1[CH2:15][CH2:14][C@H:13]([O:16][CH2:17][C:18]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 79799Tolylboronic acidHCID 522689Potassium FluorideHCID 131727184HCID 131727184, compound

Product 1

HCID 86760758HCID 86760758, compoundYield 105.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 66942082HCID 66942082, compoundCatalystHCID 10340Sodium CarbonateSolvent

Procedure

A stirred mixture of 10 g of racemic trans [3-(2-bromo-3-phenyl-allyloxy)-cyclopentyl]-carbamic acid benzyl ester, 4.7 g of p-tolylboronic acid, 160 mg of o-biphenyl dicyclohexylphosphine, 52 mg of palladium acetate, 4 g of potassium fluoride and 25 mL of anhydrous tetrahydrofuran was stirred at room temperature for 1 h then heated to 50° C. for 3h under nitrogen atmosphere. The mixture was cooled diluted with 50 mL of sodium carbonate and extracted with 3×100 mL portions of ethyl acetate. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Chromatography using a gradient of 0% to 25% ethyl acetate in hexane gave 10.8 g of product as a crystalline solid: MS (m+1)=442.3; 1H NMR (400 MHz, CDCl3) 7.35 (m, 4H), 7.1 (m, 8H), 7.0 (d, 2H), 6.6 (s, 1H), 5.1 (s, 2H), 4.7 (br s, 1H), 4.2 (s, 2H), 4.1 (m, 1H), 2.37 (s, 3H), 2.2 (m, 2H), 1.986 (m, 1H), 1.78 (m, 1H), 1.62 (m, 1H), 1.4 (m, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with 3×100 mL portions of ethyl acetate
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4bacd77ca72046e38c2ce82a37cc761b
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

Loading…