Aniline → 3-Phenylaminocyclopentanecarboxylic acid benzyl ester

HRID 1024501

反応式

HRID 1024501 の反応式
[CH2:1]([O:8][C:9]([CH:11]1[CH2:15][CH2:14][C:13](=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.C(O)(=O)C>[CH2:1]([O:8][C:9]([CH:11]1[CH2:15][CH2:14][CH:13]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 14530748Benzyl 3-oxocyclopentanecarboxylate

生成物 1

HCID 667260583-Phenylaminocyclopentanecarboxylic acid benzyl ester

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

The mixture of 3-oxocyclopentanecarboxylic acid benzyl ester (150 mg), aniline (75 mg), glacial acetic acid (200 μL), and sodium triacetoxyborohydride (230 mg) in DCM (20 mL) was stirred overnight. Upon the addition of aq. potassium carbonate (1M, 30 mL), the mixture was extracted with ethyl acetate (30 ml×2). Organic layers were combined, washed with brine, and concentrated. Flash chromatography on silica (50% ethyl acetate in hexane) gave the product as an oil: MS (m+1)=282.3.

後処理

  1. extractionthe mixture was extracted with ethyl acetate (30 ml×2)
  2. washwashed with brine
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-6d987d025dfe45028fa0b3978dae20da
出典データセット
uspto-grants-2014_05
特許番号
US08722896B2

関連ノート

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