Ethylene Glycol → HCID 86611435, compound

HRID 1360386Notes

Reaction equation

HRID 1360386 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6](I)=[CH:5][CH:4]=1.[NH:12]1[CH2:16][CH2:15][C@@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>[Cu]I.CC(O)C>[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([N:12]2[CH2:16][CH2:15][C@@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:13]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine

Product 1

HCID 86611435HCID 86611435, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

4-(Trifluoromethyl)iodobenzene (145 μl, 1.0 mmol), tert-butyl (3R)-pyrrolidin-3-ylcarbamate (0.22 g, 1.2 mmol), potassium phosphate (0.43 g, 2.0 mmol), ethylene glycol (0.11 mL, 2.0 mmol), copper(I) iodide (19 mg, 0.10 mmol) and 2-propanol (1 mL) were charged in a threaded test tube, and the mixture was stirred overnight at 80° C. The solvent was evaporated, and the residue was worked-up according to a conventional method. The obtained crude product was purified by silica gel column chromatography (15% mixed solvent of ethyl acetate/hexane) to give the title compound (0.07 g, 0.21 mmol, 21%).

Workup

  1. customThe solvent was evaporated
  2. customThe obtained crude product
  3. customwas purified by silica gel column chromatography (15% mixed solvent of ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2bce14741957413aa03031cfc2f1e07b
Source dataset
uspto-grants-2011_02
Patent number
US07879863B2

Reaction notes

Loading…