4-Methylbenzyl chloride → HCID 53256309, compound
Reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.Cl[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:1]2[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]2)=[CH:18][CH:17]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a mixture of tert-butyl (3R)-3-pyrrolidinylcarbamate (4.0 g) and 1-(chloromethyl)-4-methylbenzene (3.17 g) in DMF(40 mL) was added N-ethyl-N-isopropyl-2-propanamine (5.55 g) at ambient temperature and the resulting mixture was heated at 70° C. for four hours. The mixture was allowed to cool to ambient temperature and extracted with ethyl acetate (100 mL). The organic phase was washed with water (50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by a flash chromatography eluting with gradient solvent system (ethyl acetate-hexane from 1:4 v/v to 1:1 v/v) to give tert-butyl [(3R)-1-(4-methylbenzyl)-3-pyrrolidinyl]carbamate (4.69 g) as a pale yellow syrup.
Workup
- temperatureto cool to ambient temperature
- extractionextracted with ethyl acetate (100 mL)
- washThe organic phase was washed with water (50 mL) and brine (50 mL)
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by a flash chromatography
- washeluting with gradient solvent system (ethyl acetate-hexane from 1:4 v/v to 1:1 v/v)
Sources & evidence
- ORD record
- ord-5945a60561544ab6be9609273fa7c69e
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557127B2
Reaction notes
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