4-Cyclohexylphenol → (S)-2-(4-cyclohexyl-phenoxymethyl)-5-propyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237812Notes

Reaction equation

HRID 237812 reaction equation
[CH:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH2:12][C@H:13]3[O:17][C:16]([NH2:18])=[N:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1O[C@H]1CCl.[CH:26]1([C:32]2C=C[C:35]([OH:38])=[CH:34][CH:33]=2)CCCC[CH2:27]1.C(OC)(=O)C#CCCC>C(O)C>[CH:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH2:12][C@H:13]3[O:17][C:16]4=[N:18][C:35](=[O:38])[CH:34]=[C:33]([CH2:32][CH2:26][CH3:27])[N:15]4[CH2:14]3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 143274-CyclohexylphenolHCID 87860Methyl 2-hexynoateHCID 2734062(-)-EpichlorohydrinHCID 66875140(S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 25069508(S)-2-(4-cyclohexyl-phenoxymethyl)-5-propyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-oneYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-5-(4-Cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (0.37 g, 1.35 mmol), prepared in accordance with the procedures in Steps 1 and 2 of Example 1 and starting from R-epichlorohydrin and 4-cyclohexylphenol, was dissolved in ethanol (6 mL). Methyl 2-hexynoate (0.34 g, 2.70 mmol) was then added and the reaction mixture was heated at reflux for 24 hrs and then cooled to room temperature. The resulting crystalline solid was isolated by filtration, washed with heptane 3 times, and dried under vacuum to afford 135 mg (27% yield) of (S)-2-(4-cyclohexyl-phenoxymethyl)-5-propyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one as a white solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 24 hrs
  3. customThe resulting crystalline solid was isolated by filtration
  4. washwashed with heptane 3 times
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d623adc7489c40cd87bbfec000983a93
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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