1-Octyne → 5-(Oct-1-ynyl)-2-tritylisoindoline

HRID 710283

反応式

HRID 710283 の反応式
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:5]2.[CH:30]#[C:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>CN(C=O)C.[Cu]I>[C:30]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:11]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:5]2)#[C:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

参加物

5

反応物 2

HCID 123701-OctyneHCID 667262485-Iodo-2-tritylisoindoline

生成物 1

HCID 667262275-(Oct-1-ynyl)-2-tritylisoindoline収率 89%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of the product of Step C (0.2 g; 0.41 mmol), 1-octyne (0.091 ml; 0.62 mmol), Cl2Pd(PPh3)2 (0.02 g; 0.028 mmol) and CuI (0.005 g; 0.026 mmol) in anhydrous DMF (2 ml) was degassed under reduced pressure and saturated with dry N2. After addition of DIPEA (0.5 ml), the resulting mixture was stirred overnight at room temperature under N2. The solvents were removed in vacuo and the residue was diluted to 15 ml with EtOAc and washed with 5% citric acid, 5% NaHCO3, H2O, brine and dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by FCC (SiO2; hexane/EtOAc; 9:1) to give the title compound (0.17 g; 89%) as a colourless syrup. 1H-NMR (CDCl3) 0.93 (m, 3H); 1.34-1.64 (m, 8H); 2.4 (tr, 2H, J=7.1 Hz); 3.94 (s, 4H); 7.0-7.64 (m, 18H).

後処理

  1. customwas degassed under reduced pressure and saturated with dry N2
  2. additionAfter addition of DIPEA (0.5 ml)
  3. customThe solvents were removed in vacuo
  4. additionthe residue was diluted to 15 ml with EtOAc
  5. washwashed with 5% citric acid, 5% NaHCO3, H2O, brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness under reduced pressure
  9. customthe residue was purified by FCC (SiO2; hexane/EtOAc; 9:1)

出典と根拠

ORDレコード
ord-927d2a5d3eac469b98766d946bf5847e
出典データセット
uspto-grants-2015_11
特許番号
US09181182B2

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