Aniline → 3-Phenylaminocyclopentanecarboxylic acid benzyl ester

HRID 1024501Notes

Reaction equation

HRID 1024501 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 667260583-Phenylaminocyclopentanecarboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-6d987d025dfe45028fa0b3978dae20da
Source dataset
uspto-grants-2014_05
Patent number
US08722896B2

Reaction notes

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