Triphosgene → (7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]hexahydropyrrolo[1,2-a]-pyrazine-2(1H)-carbonyl chloride
Reaction equation
[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:19][N:14]4[CH2:15][CH2:16][NH:17][CH2:18][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[Cl:20][C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:19][N:14]4[CH2:15][CH2:16][N:17]([C:21]([Cl:20])=[O:23])[CH2:18][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the product from Example 54F (73 mg, 0.28 mmol) in dichloromethane (2.5 mL) was added triphosgene (32 mg, 0.106 mmol), and the resulting mixture was stirred at ambient temperature for 16 hours. The mixture was diluted with dichloromethane (10 mL) and washed by 10% aqueous NaHCO3 solution (5 mL). The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the title compound.
Workup
- washwashed by 10% aqueous NaHCO3 solution (5 mL)
- extractionThe organic extract
- dry with materialwas dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-3c9feca74d4e4f61ad2d7cf7e1fe30b2
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669255B2
Reaction notes
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