Methyl iodide → HCID 11998562, compound
Reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[N:13]1([C:19]2[S:20][C:21]3[C:27](=[O:28])[CH2:26][CH2:25][CH2:24][C:22]=3[N:23]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.CI>C1COCC1>[CH3:1][CH:26]1[CH2:25][CH2:24][C:22]2[N:23]=[C:19]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[S:20][C:21]=2[C:27]1=[O:28]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of N,N-diisopropylamine (0.60 g, 0.83 mL, 5.9 mmol) in dry THF (5 mL) was cooled to −78° C. and n-butyllithium (2.36 mL, 2.5M in hexane, 5.9 mmol) was added dropwise. The reaction mixture was allowed to warm to 0° C., stirred for 15 minutes and cooled to −78° C. A suspension of Example 6 (1.4 g, 5.9 mmol) in THF (5 mL) was added slowly. The reaction mixture was warmed to 0° C. and stirred for 10 min at 0° C. before dropwise addition of methyl iodide (0.84 g, 0.37 mL, 5.9 mmol). A solid formed immediately. The reaction mixture was allowed to warm slowly to r.t. The solid was filtered, washed with THF and then purified by column chromatography (SiO2, 1:3 EtOAc/hexane) to give the title compound (0.20 g, 13%) as a white solid. δH (DMSO-d6) 3.70 (4H, t, J 4.9 Hz), 3.54 (4H, t, J 4.9 Hz), 2.80-2.72 (2H, m), 2.55-2.45 (1H, m), 2.15-2.09 (1H, m), 1.82-1.72 (1H, m), 1.10 (3H, d, J 6.9 Hz). LCMS (ES+) 253.0 (M+H)+.
Workup
- temperaturecooled to −78° C
- temperatureThe reaction mixture was warmed to 0° C.
- customA solid formed immediately
- temperatureto warm slowly to r.t
- filtrationThe solid was filtered
- washwashed with THF
- custompurified by column chromatography (SiO2, 1:3 EtOAc/hexane)
Sources & evidence
- ORD record
- ord-dad386980cd1498aadfdcc8d83ec6879
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07888344B2
Reaction notes
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