4-Cyclohexylphenol → (S)-2-(4-Cyclohexyl-phenoxymethyl)-6-isopropyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237822Notes

Reaction equation

HRID 237822 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.C1(C2C=CC(O)=CC=2)CCCCC1.C([O:41][C:42](=O)[CH:43]([CH:47]=O)[CH:44]([CH3:46])[CH3:45])C>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:42](=[O:41])[C:43]([CH:44]([CH3:46])[CH3:45])=[CH:47][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 2734062(-)-EpichlorohydrinHCID 13379358Ethyl 2-formyl-3-methylbutanoateHCID 66875140(S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 25071112(S)-2-(4-Cyclohexyl-phenoxymethyl)-6-isopropyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-oneYield 22.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (0.48 g, 1.74 mmol) (prepared in accordance with the procedures described in Steps 1 and 2 of Example 1 and starting from R-epichlorohydrin and 4-cyclohexylphenol) in ethanol (16 mL) was added 2-formyl-3-methyl-butyric acid ethyl ester (0.33 g, 2.1 mmol). The reaction mixture was heated at reflux for 24 hours. It was then concentrated to remove solvent and loaded on silica gel column. Chromatography with (1-5%) 2-propanol/methylene chloride gave 0.144 g of the title compound. [α]D25 −15.80 (c 0.5, CHCl3).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 24 hours
  3. concentrationIt was then concentrated
  4. customto remove solvent

Sources & evidence

ORD record
ord-4f6f099cd99442b2936bc43dabe67191
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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