Ethyl pent-2-yn-1-oate → (S)-5-ethyl-2-(5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-yloxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one
Reaction equation
[CH:1]1[C:13]2[CH2:12][CH:11]3[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]3)[C:5]=2[CH:4]=[CH:3][C:2]=1[O:14][CH2:15][C@H:16]1[O:20][C:19]([NH2:21])=[N:18][CH2:17]1.C1O[C@H]1CCl.[CH:27]1[C:39]2CC3C(CCCC3)[C:31]=2[CH:30]=C[C:28]=1[OH:40].C(OCC)(=O)C#CCC>C(O)C>[CH2:31]([C:39]1[N:18]2[CH2:17][C@@H:16]([CH2:15][O:14][C:2]3[CH:3]=[CH:4][C:5]4[CH:6]5[CH:11]([CH2:10][CH2:9][CH2:8][CH2:7]5)[CH2:12][C:13]=4[CH:1]=3)[O:20][C:19]2=[N:21][C:28](=[O:40])[CH:27]=1)[CH3:30]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (S)-5-(5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-yloxymethyl)-4,5-dihydro-oxazol-2-ylamine (16 mg, 0.055 mmol), prepared in accordance with the procedures in Steps 1 and 2 of Example 1 and starting from R-epichlorohydrin and 5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-ol (prepared by the same procedure as in Step 1 of Example 19), in ethanol (2 mL) was added ethyl 2-pentynoate (4.2 mg, 0.065 mmol). The reaction mixture was heated at reflux for 14 hrs and then cooled to room temperature. The reaction mixture was concentrated and then loaded onto a silica gel column, and eluted with 2-6% methanol/methylene chloride to afford 8 mg of (S)-5-ethyl-2-(5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-yloxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one.
Workup
- temperatureThe reaction mixture was heated
- temperatureat reflux for 14 hrs
- concentrationThe reaction mixture was concentrated
- washeluted with 2-6% methanol/methylene chloride
Sources & evidence
- ORD record
- ord-d2acc16e602746e5999cb8db8b1fd42e
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642603B2
Reaction notes
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