Tetrahydrofuran → 2-(4-{4-[3-(2-Methoxybenzyloxy)propoxy]phenyl}piperidin-3-yloxymethyl)-1-(3-methoxypropyl)-1H-indole

HRID 1712295ノート

反応式

HRID 1712295 の反応式
CS(N1C2C(=CC=CC=2)C=C1[CH2:14][O:15][CH:16]1[CH:21]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[O:40][CH3:41])=[CH:24][CH:23]=2)[CH2:20][CH2:19][N:18](C(OCC2C=CC=CC=2)=O)[CH2:17]1)(=O)=O.[F-].C([N+:57]([CH2:66][CH2:67][CH2:68][CH3:69])([CH2:62][CH2:63][CH2:64][CH3:65])[CH2:58][CH2:59][CH2:60]C)CCC.[O:70]1CCC[CH2:71]1>>[CH3:41][O:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][O:32][CH2:31][CH2:30][CH2:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([CH:21]2[CH2:20][CH2:19][NH:18][CH2:17][CH:16]2[O:15][CH2:14][C:66]2[N:57]([CH2:58][CH2:59][CH2:60][O:70][CH3:71])[C:62]3[C:68]([CH:67]=2)=[CH:69][CH:65]=[CH:64][CH:63]=3)=[CH:23][CH:24]=1

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 68499233HCID 68499233、化合物

生成物 1

HCID 685004622-(4-{4-[3-(2-Methoxybenzyloxy)propoxy]phenyl}piperidin-3-yloxymethyl)-1-(3-methoxypropyl)-1H-indole

実験手順

The solution of 0.160 g of benzyl 3-(1-methanesulphonyl-1H-indol-2-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 11 ml of tetrahydrofuran is admixed with 0.44 ml of tetrabutylammonium fluoride solution (1M in tetrahydrofuran) and stirred at reflux over 20 hours. The reaction mixture is cooled, poured onto brine (40 ml) and extracted with ethyl acetate (2×40 ml). The organic phases are washed with brine (1×40 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as an orange oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.18 (1:2 EtOAc-heptane); Rt=26.90 (II).

後処理

  1. temperatureat reflux over 20 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto brine (40 ml)
  4. extractionextracted with ethyl acetate (2×40 ml)
  5. washThe organic phases are washed with brine (1×40 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-71b7c1c2ece549f69853ca721e38e226
出典データセット
uspto-grants-2010_09
特許番号
US07790715B2

反応ノート

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