Acetic Anhydride → HCID 54082237、化合物

HRID 22288

反応式

HRID 22288 の反応式
[C:1]1(=[O:13])[C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[NH:5][C:4]=2[CH2:3][CH2:2]1.[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([CH:27]=O)[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([N-]C(C)C)(C)C.[Li+].C(OC(=O)C)(=O)C>C1COCC1>[C:15]1([CH2:14][N:21]2[CH2:26][CH2:25][CH:24]([CH:27]=[C:2]3[CH2:3][C:4]4[NH:5][C:6]5[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=5[C:12]=4[C:1]3=[O:13])[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 7918Acetic AnhydrideHCID 895841-Benzylpiperidine-4-carbaldehydeHCID 2724682Lithium diisopropylamideHCID 64246693,4-Dihydrocyclopenta(b)indol-1(2H)-one

生成物 1

HCID 54082237HCID 54082237、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a mixture of 1,2,3,4-tetrahydrocyclopent[b]-indol-1-one (440 mg, 2.6 mmol) and 1-benzylpiperidine-4-carboxaldehyde (581 mg, 2.86 mmol) in 90 ml dry THF was added 5.4 mmol of lithium diisopropylamide at -78° C. The mixture was stirred at -78° C. for 30 minutes, then warmed up to 0° C. for 1.5 hours, and then to r.t. for 15 minutes. Acetic anhydride (0.265 g, 2.6 mmol) was added, the mixture was stirred at r.t. for 1.5 hours and quenched ammonium chloride, water and extracted with chloroform. The organic layer was dried, concentrated, and purified through silica gel to give the title compound. 1HNMR (CDCl3)δ 1.45-1.7 (m, 3H), 1.8-2.3 (m, 4H), 2.8-3.0 (m, 2H), 3.46 (s, 2H), 3.55 (s, 2H), 6.5 (m, 1H), 7.1-7.4 (m, 8H), 7.9 (m, 1H), 9.2 (s, 1H) ppm.

後処理

  1. temperaturewarmed up to 0° C. for 1.5 hours
  2. waitto r.t. for 15 minutes
  3. stirringthe mixture was stirred at r.t. for 1.5 hours
  4. customquenched ammonium chloride, water
  5. extractionextracted with chloroform
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. custompurified through silica gel

出典と根拠

ORDレコード
ord-38dbbafc6f744e7f8c4c06aaaa9e7d7c
出典データセット
uspto-grants-1995_06
特許番号
US05428043

関連ノート

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