Pyrrolidine → 2-[3-(Methyloxy)-4-nitrophenyl]-5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazole

HRID 419339ノート

反応式

HRID 419339 の反応式
Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([O:17][CH3:18])[CH:9]=2)=[N:6][N:7]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCOCC1>[CH3:18][O:17][C:10]1[CH:9]=[C:8]([C:5]2[O:4][C:3]([CH2:2][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[N:7][N:6]=2)[CH:13]=[CH:12][C:11]=1[N+:14]([O-:16])=[O:15]

参加物

4

反応物 2

HCID 31268PyrrolidineHCID 594526612-(Chloromethyl)-5-[3-(methyloxy)-4-nitrophenyl]-1,3,4-oxadiazole

生成物 1

HCID 594529402-[3-(Methyloxy)-4-nitrophenyl]-5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazole収率 99%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To 2-(chloromethyl)-5-[3-(methyloxy)-4-nitrophenyl]-1,3,4-oxadiazole (Example 26, step C) (1.01 g, 3.75 mmol) in dioxane (10 mL) was added pyrrolidine (0.800 mL, 9.58 mmol). The reaction was stirred at rt overnight. Upon completion by TLC, the reaction mixture was treated with BOC-anhydride (0.371 g, 1.69 mmol) and cooled to 0° C. The mixture was treated with TEA (0.279 mL, 2.00 mmol). Purification by flash chromatography provided the title compound of step A (1.13 g, 3.70 mmol, 99%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.64-1.72 (m, 4H), 2.56 (br. s., 4H), 3.92-3.96 (m, 2H), 3.98-4.02 (m, 3H), 7.64-7.69 (m, 1H), 7.79 (br. s., 1H), 8.01-8.06 (m, 1H).

後処理

  1. temperaturecooled to 0° C
  2. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-5d323fd7674d46148f536f01b15bd23c
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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