Fenproporex hydrochloride → n-{2-[(8r)-2-Methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl]ethyl}acetamide

HRID 887802Notes

Reaction equation

HRID 887802 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][C:7]3[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[C:8]=32)=[N:3]1.CC(NCCC#N)CC1C=CC=CC=1.Cl>CCCCCC.C(O)C>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][C:7]3[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[C:8]=32)=[N:3]1

Participants

4

Reactant 2

HCID 161245Fenproporex hydrochlorideHCID 59145872N-[2-(2-methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl)ethyl]acetamide

Product 1

HCID 59145855n-{2-[(8r)-2-Methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl]ethyl}acetamideYield 51.4%

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent2×

Procedure

N-[2-(2-Methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl)ethyl]acetamide (about 70 mg) was fractionated by high performance liquid chromatography (instrument: Prep LC 2000 (manufactured by Nihon Waters K.K.), column: CHIRALPAK AD (50 mm ID×500 mm L, manufactured by Dicel Chemical Industries, Ltd.), mobile phase: hexane/ethanol=90/10, flow rate: 80 mL/min, column temperature: room temperature, sample concentration: 1.0 mg/mL (hexane/ethanol=90/10), injection amount: about 35 mg). A fraction solution containing an optically active compound having a longer retention time under the above-mentioned high performance liquid chromatography conditions was concentrated. The concentrate was re-dissolved in ethanol, and concentrated to dryness. Hexane was further added, and the mixture was concentrated to dryness again to give the title compound (36 mg, 99% ee). The enantiomer excess (ee) was measured by high performance liquid chromatography (column: CHIRALPAK AD-H (4.6 mm ID×250 mm L, manufactured by Dicel Chemical Industries, Ltd.), mobile phase: hexane/ethanol=90/10, flow rate: 1.0 mL/min, column temperature: room temperature, sample concentration: 1 mg/mL (hexane/ethanol=90/10), injection volume: 10 μL).

Workup

  1. additionA fraction solution containing an optically active compound
  2. concentrationwas concentrated
  3. dissolutionThe concentrate was re-dissolved in ethanol
  4. concentrationconcentrated to dryness
  5. additionHexane was further added
  6. concentrationthe mixture was concentrated to dryness again

Sources & evidence

ORD record
ord-51445e40bbaa474992374927bbea297c
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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