1,2-Dichloroethane → {4-[4-(Pyrrolidin-1-ylcarbonyl)-1,3-oxazol-2-yl]phenyl}methanol

HRID 1716860ノート

反応式

HRID 1716860 の反応式
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=2)=[CH:5][CH:4]=1.C(Cl)CCl.[CH:21]1[CH:22]=CC2N(O)N=[N:27][C:25]=2[CH:26]=1.N1CCCC1>CN(C=O)C>[N:27]1([C:14]([C:12]2[N:13]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH2:2][OH:1])=[CH:8][CH:7]=3)[O:10][CH:11]=2)=[O:16])[CH2:22][CH2:21][CH2:26][CH2:25]1

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 575501932-[4-(Hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylic acid

生成物 1

HCID 57550216{4-[4-(Pyrrolidin-1-ylcarbonyl)-1,3-oxazol-2-yl]phenyl}methanol収率 84%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A stirred solution of 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylic acid (0.99 g, 4.5 mmol) in DMF was treated sequentially with EDC (1.04 g, 5.4 mmol), HOBt (0.67 g, 5.0 mmol and pyrrolidine (0.35 g, 5.0 mmol), stirred at 80° C. for 4 hours and evaporated to dryness. The resultant residue was dissolved in EtOAc and water. The layers were separated and the organic layer was washed successively with 1M HCl, water, saturated NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure The resultant residue was purified by flash chromatography (silica, EtOAc:hexanes 25%) to give the title product in 84% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 273 (MH+).

後処理

  1. customevaporated to dryness
  2. dissolutionThe resultant residue was dissolved in EtOAc
  3. customThe layers were separated
  4. washthe organic layer was washed successively with 1M HCl, water, saturated NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure The resultant residue
  7. customwas purified by flash chromatography (silica, EtOAc:hexanes 25%)

出典と根拠

ORDレコード
ord-c721f8f882734a99be033433945632e8
出典データセット
uspto-grants-2010_09
特許番号
US07803825B2

反応ノート

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