Aniline → 3-Phenylaminocyclopentanecarboxylic acid benzyl ester

HRID 1024501노트

반응식

HRID 1024501 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 667260583-Phenylaminocyclopentanecarboxylic acid benzyl ester

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-6d987d025dfe45028fa0b3978dae20da
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722896B2

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