Water → (4R)-{2-[5-(5-Cyclohexylpent-1-ynyl)thiophen-2-yl]}ethyl-4-methyloxazolidin-2-one

HRID 1063440Notes

Reaction equation

HRID 1063440 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][CH2:8][N:9]2[C@H:13]([CH3:14])[CH2:12][O:11][C:10]2=[O:15])=[CH:4][CH:3]=1.[CH:16]1([CH2:22][CH2:23][CH2:24][C:25]#[CH:26])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C.O>CN(C)C=O.[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>[CH:16]1([CH2:22][CH2:23][CH2:24][C:25]#[C:26][C:2]2[S:6][C:5]([CH2:7][CH2:8][N:9]3[C@H:13]([CH3:14])[CH2:12][O:11][C:10]3=[O:15])=[CH:4][CH:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15172912(Pent-4-yn-1-yl)cyclohexaneHCID 69338201(4R)-[2-(5-Bromothiophen-2-yl)]ethyl-4-methyloxazolidin-2-one

Product 1

HCID 69338073(4R)-{2-[5-(5-Cyclohexylpent-1-ynyl)thiophen-2-yl]}ethyl-4-methyloxazolidin-2-oneYield 82%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

(4R)-[2-(5-Bromothiophen-2-yl)]ethyl-4-methyloxazolidin-2-one (450 mg, 1.55 mmol) obtained in Example 1 (g) was dissolved in dimethylformamide (4.5 ml), and 5-cyclohexylpent-1-yne (50% xylene solution) (1.4 g, 4.65 mmol), triethylamine (2.16 ml, 15.5 mmol), copper (I) iodide (30 mg, 0.16 mmol) and dichlorobis(triphenylphosphine)palladium (109 mg, 0.16 mmol) were added thereto, and then the reaction mixture was stirred for 2 hours at 80° C. under a nitrogen atmosphere. The reaction solution was poured into water, extracted with ethyl acetate, and the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution. After the ethyl acetate layer was dried over anhydrous sodium sulfate, the solvent was concentrated in vacuo, and the residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=4:1-3:2) to afford the title compound (56 mg, 82% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialAfter the ethyl acetate layer was dried over anhydrous sodium sulfate
  4. concentrationthe solvent was concentrated in vacuo
  5. customthe residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=4:1-3:2)

Sources & evidence

ORD record
ord-e427cc11050a4e17a0ad29916b6eb517
Source dataset
uspto-grants-2005_11
Patent number
US06964976B2

Reaction notes

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