Diazomethane → HCID 58155344, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@:8]2([CH3:24])[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:12](=[O:23])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH:25](N)(C)C.[Li].[N+](=C)=[N-]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C@@:8]2([CH3:24])[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:12](=[O:23])[C@H:11]([CH3:25])[O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -75 °C
Procedure
A dried flask was charged under an argon atmosphere with a solution of (R)-5-(3-bromo-phenyl)-4-(4-methoxy-benzyl)-5-methyl-morpholin-3-one (600 mg, 1.5 mmol) in tetrahydrofuran (16 ml) which was cooled to −75° C. Lithium isopropylamine (1.54 ml, 3 mmol) was added, and after the addition of diazomethane (502 mg, 3.5 mmol) the reaction was complete. For the workup, the cold reaction mixture was quenched with a saturated ammonium chloride solution (15 ml) and extracted with a mixture of dichloromethane (40 ml) and water (15 ml). The organic layer was dried over sodium sulfate and evaporated to yield the crude (2S,5R)-5-(3-bromo-phenyl)-4-(4-methoxy-benzyl)-2,5-dimethyl-morpholin-3-one as a brownish oil which was engaged in the next step without further purification. Mass (calculated) C20H22BrNO3 [404.307]; (found) [M+H]+=404, [M+2-H]+=406.
Workup
- customFor the workup, the cold reaction mixture
- customwas quenched with a saturated ammonium chloride solution (15 ml)
- extractionextracted with a mixture of dichloromethane (40 ml) and water (15 ml)
- dry with materialThe organic layer was dried over sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-7832fbf9dc3d42a2854e08d10aad3b14
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188079B2
Reaction notes
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