Methyl iodide → Methyl (R)-3-((tert-butoxycarbonyl)(methyl)amino)-2,3-dihydro-1H-indene-5-carboxylate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:24]I>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH3:24])[C@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (R)-methyl 3-(tert-butoxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate (600 mg, 2.062 mmol, 1.0 eq.) in dry DMF (2 ml) was added to a stirred suspension of NaH (118 mg, 2.474 mmol, 1.2 eq., 50% in mineral oil) in DMF (3 ml) at 0° C. MeI (322 μl, 5.15 mmol, 2.5 eq.) was added to the reaction mixture at same temperature and it was stirred at RT for 2 h. After completion of the reaction (monitored by TLC), the reaction mixture diluted with ice-cold water (50 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with water (50 ml) and brine (50 ml), and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give the crude product as a brown sticky solid which was used in the next step without further purification. Yield: 90% (566 mg, 1.855 mmol).
Workup
- customAfter completion of the reaction (monitored by TLC)
- extractionextracted with ethyl acetate (2×50 ml)
- washThe combined organic layers were washed with water (50 ml) and brine (50 ml)
- dry with materialdried over sodium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-a64148987cc6454898e6558521512030
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455475B2
Reaction notes
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