Methyl iodide → HCID 54406880, compound
Reaction equation
[C:1]([NH:11][C@@H:12]([CH3:22])[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:23]I.[H-].[Na+]>CN(C=O)C>[C:1]([N:11]([C@@H:12]([CH3:22])[C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)[CH3:23])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 7.5 °C
Procedure
A solution of (S)-(-)-N-carbobenzyloxy-α-methyl-4-nitrobenzylamine (8.2 gm, 28 mmol) and methyl iodide (2.6 mL, 42 mmol) in DMF (50 mL) was cooled under nitrogen in an ice bath to 5-10° C. and sodium hydride (60% suspension in mineral oil) (1.2 gm, 31 mmol) was added in portions over 15 min while maintaining the temperature at 5-10° C. The reaction was stirred for 1 hr and then slowly quenched into a mixture of ice water, 2N hydrochloric acid (20 mL) and ether and the layers were separated. The ether layer was washed with water and brine and the aqueous layers were consecutively extracted with a second portion of ether. The pooled ether layers were dried over sodium sulfate and evaporated. The residue was purified by flash chromatography using 10-30% ethyl acetate/hexanes to give 6.6 gm (77%) of the title compound. [α]D (EtOH)=-97°.
Workup
- customslowly quenched into a mixture of ice water, 2N hydrochloric acid (20 mL) and ether
- customthe layers were separated
- washThe ether layer was washed with water and brine
- extractionthe aqueous layers were consecutively extracted with a second portion of ether
- dry with materialThe pooled ether layers were dried over sodium sulfate
- customevaporated
- customThe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-c48c07716b9e4b96a5201d5d6a650188
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05952321
Reaction notes
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