Ethyl pent-2-yn-1-oate → (S)-2-(4-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-5-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237806Notes

Reaction equation

HRID 237806 reaction equation
[CH:1]12[CH:9]([C:10]3[CH:23]=[CH:22][C:13]([O:14][CH2:15][C@H:16]4[O:20][C:19]([NH2:21])=[N:18][CH2:17]4)=[CH:12][CH:11]=3)[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2.C1O[C@H]1CCl.C12[CH:37]([C:38]3C=C[C:41]([OH:44])=[CH:40][CH:39]=3)C(CCC1)CCC2.C(OCC)(=O)C#CCC>C(O)C>[CH:1]12[CH:9]([C:10]3[CH:23]=[CH:22][C:13]([O:14][CH2:15][C@H:16]4[O:20][C:19]5=[N:21][C:41](=[O:44])[CH:40]=[C:39]([CH2:38][CH3:37])[N:18]5[CH2:17]4)=[CH:12][CH:11]=3)[CH:5]([CH2:4][CH2:3][CH2:2]1)[CH2:6][CH2:7][CH2:8]2

Participants

6

Reactant 4

HCID 99169Ethyl pent-2-yn-1-oateHCID 2734062(-)-EpichlorohydrinHCID 443594624-(Bicyclo[3.3.1]nonan-9-yl)phenolHCID 68527534(S)-5-(4-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 25074225(S)-2-(4-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-5-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-5-(4-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (0.26 g, 0.828 mmol), prepared in accordance with the procedures as set forth in Steps 1 and 2 of Example 1 and starting from R-epichlorohydrin and 4-bicyclo[3.3.1]non-9-yl phenol (prepared with the same procedure as set forth in steps 1 and 2 of Example 20), in ethanol (5 mL) was added ethyl 2-pentynoate (0.157 g, 1.24 mmol). The reaction mixture was heated at reflux for 14 hrs and then cooled to room temperature. The reaction mixture was concentrated and loaded onto a silica gel column, and eluted with 4-6% methanol/methylene chloride to afford 120 mg of (S)-2-(4-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-5-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one. [α]D25 −36.89 (c 0.501, CHCl3).

Workup

  1. customprepared with the same procedure
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 14 hrs
  4. concentrationThe reaction mixture was concentrated
  5. washeluted with 4-6% methanol/methylene chloride

Sources & evidence

ORD record
ord-ca1c05f396ca4a5ea9058866f4a13a3d
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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