Trifluoroacetic acid → 3-[4-[2-(2-Oxopyrrolidin-1-yl)ethoxy]benzyl]-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene

HRID 1700774ノート

反応式

HRID 1700774 の反応式
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[C:19]3[CH:40]=[CH:39][CH:38]=[CH:37][C:20]=3[S:21][C:22]=2[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:25][CH:24]=2)=O)=[CH:12][CH:11]=1.[BH4-].[Li+].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C1COCC1.CO.[Cl-].[Na+].O.ClCCl>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:18]2[C:19]3[CH:40]=[CH:39][CH:38]=[CH:37][C:20]=3[S:21][C:22]=2[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:25][CH:24]=2)=[CH:12][CH:11]=1

参加物

8

反応物 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 4148881Lithium borohydrideHCID 183185242-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]-benzo[b]thiophen-3-yl 4-[2-(2-Oxopyrrolidin-1-yl)ethoxy]-phenyl Ketone

生成物 1

HCID 183185073-[4-[2-(2-Oxopyrrolidin-1-yl)ethoxy]benzyl]-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene収率 23.1%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 21899815MeOH tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 4-[2-(2-oxopyrrolidin-1-yl)ethoxy]phenyl ketone (120 mg) was dissolved in THF/MeOH (3.0/0.3 mL) and treated with lithium borohydride (40 mg) in one portion and allowed to stir at ambient temperature for 4 h. The reaction mixture was diluted with brine (30 mL) and extracted with dichloromethane (20 mL×3). The combined organic layers were dried with sodium sulfate and concentrated in vacuo to give the crude alcohol. This material was dissolved in dichloromethane (3.0 mL), treated with triethylsilane (0.25 mL) and trifluroacetic acid (0.2 mL) sequentially, allowed to stir at ambient temperature for 2 h, and concentrated under reduced pressure. The residue was extracted with -dichloromethane (20 mL×3) from saturated aqueous sodium bicarbonate (30 mL). The combined organic layers were dried with sodium sulfate and concentrated. Chromatography with Et3N:MeOH:EtOAc (5:5:90) afforded the title compound (27 mg).

後処理

  1. extractionextracted with dichloromethane (20 mL×3)
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give the crude alcohol
  5. stirringto stir at ambient temperature for 2 h
  6. concentrationconcentrated under reduced pressure
  7. extractionThe residue was extracted with -dichloromethane (20 mL×3) from saturated aqueous sodium bicarbonate (30 mL)
  8. dry with materialThe combined organic layers were dried with sodium sulfate
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-3c54582c75cb4ec991260284e880c354
出典データセット
uspto-grants-2002_02
特許番号
US06350774B1

反応ノート

読み込み中…