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

HRID 1063440ノート

反応式

HRID 1063440 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

(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).

後処理

  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)

出典と根拠

ORDレコード
ord-e427cc11050a4e17a0ad29916b6eb517
出典データセット
uspto-grants-2005_11
特許番号
US06964976B2

反応ノート

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