Hexane ethanol diethylamine → (s)-n-[2-(2-Methyl-7,8-dihydro-6h-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]propionamide

HRID 883233Notes

Reaction equation

HRID 883233 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:13]3[CH:12]([CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])[CH2:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1.CCCCCC.C(O)C.C(NCC)C>>[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C@H:12]([CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])[CH2:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

3

Reactant 2

HCID 21881120Hexane ethanol diethylamineHCID 23725514N-[2-(2-Methyl-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]propionamide

Product 1

HCID 23634404(s)-n-[2-(2-Methyl-7,8-dihydro-6h-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]propionamideYield 47.8%

Procedure

Racemic N-[2-(2-methyl-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]propionamide (96 mg, 0.353 mmol) was fractionated by high performance liquid chromatography (instrument: Prep LC 2000 (manufactured by Nihon Waters K.K.), column: CHIRALPAK AS (50 mmID×500 mL, manufactured by Daicel Chemical Industries, Ltd.), mobile phase: hexane/ethanol/diethylamine=94/6/0.1, flow rate: 60 mL/min, column temperature: 30° C., sample concentration: 1.61 mg/mL, injection weight: 48 mg). A fraction containing an optically active compound having a shorter 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 added again, and the mixture was concentrated to dryness to give the title compound (46 mg, 99.9% ee). Enantiomer excess (ee) was measured by high performance liquid chromatography (column: CHIRALPAK AS (4.6 mmID×250 mL, manufactured by Daicel Chemical Industries, Ltd.), mobile phase: hexane/ethanol/diethylamine=95/5/0.1, flow rate: 0.5 mL/min, column temperature: 30° C., sample concentration: 0.62 mg/mL (hexane/ethanol), injection volume: 10 μL).

Workup

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

Sources & evidence

ORD record
ord-ccbb2f9a1672450d94f14b374944ff52
Source dataset
uspto-grants-2012_08
Patent number
US08236837B2

Reaction notes

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