Cyclopentanone → HCID 11619765、化合物

HRID 734797ノート

反応式

HRID 734797 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]3[CH:29]=[CH:28][C:19]([O:20][CH2:21][CH2:22][NH:23][CH2:24][CH:25]4[CH2:27][CH2:26]4)=[CH:18][CH:17]=3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[C:30]1(=O)[CH2:34][CH2:33][CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(O)=O.C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:19]([O:20][CH2:21][CH2:22][N:23]([CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[CH2:24][CH:25]4[CH2:27][CH2:26]4)=[CH:28][CH:29]=3)=[N:12][CH:13]=2)=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 8452Cyclopentanone2 回HCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydride2 回HCID 69065035HCID 69065035、化合物

生成物 1

HCID 11619765HCID 11619765、化合物

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 80.6 mg (0.20 mmol) of (2-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]phenoxy}ethyl)cyclopropylmethylamine, 35 μL (0.40 mmol) of cyclopentanone, and one drop of AcOH in 10 mL of THF was stirred for 15 minutes. 169.5 mg (0.80 mmol) of sodium triacetoxyborohydride was added and the mixture was stirred for 24 hours at RT. A further 17.5 μL of cyclopentanone and 85 mg of sodium triacetoxyborohydride were added and the mixture was again stirred for 24 hours at RT. The reaction mixture was diluted with water, made basic with saturated aqueous potassium carbonate solution, and the aqueous phase was extracted with EtOAc. The combined organic phases were dried over sodium sulfate and evaporated down in vacuo. The crude product was purified by column chromatography (silica gel, EtOAc/MeOH/conc. aqueous ammonia 98:2:0.2) and stirred with DIPE. Yield: 22 mg (23% of theoretical); C30H31ClN2O (M=471.033); calc.: molpeak (M+H)+: 471/473 (Cl); found: molpeak (M+H)+: 471/473 (Cl); HPLC-MS: 5.83 minutes (method B).

後処理

  1. stirringthe mixture was stirred for 24 hours at RT
  2. stirringthe mixture was again stirred for 24 hours at RT
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customevaporated down in vacuo
  6. customThe crude product was purified by column chromatography (silica gel, EtOAc/MeOH/conc. aqueous ammonia 98:2:0.2)
  7. stirringstirred with DIPE
  8. custom5.83 minutes (method B)

出典と根拠

ORDレコード
ord-b9a5ad4193e344839ac097b0b9c67ffa
出典データセット
uspto-grants-2009_09
特許番号
US07592358B2

反応ノート

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