Methyl iodide → HCID 90064484, compound

HRID 528505Notes

Reaction equation

HRID 528505 reaction equation
[O:1]=[C:2]1[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][O:13][C:7]3=[CH:6][C:5]=2[CH2:4][N:3]1[CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1.O1CCC[CH2:30]1.C([N-]C(C)C)(C)C.[Li+].IC>CCCCCCC.O.C(OCC)(=O)C>[CH3:30][CH:4]1[C:5]2[CH:6]=[C:7]3[O:13][CH2:12][O:11][C:8]3=[CH:9][C:10]=2[C:2](=[O:1])[N:3]1[CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 90064483HCID 90064483, compound

Product 1

HCID 90064484HCID 90064484, compoundYield 46.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
-12.5 °C

Procedure

To a reaction vessel, 30 g (0.077 mol) compound XII and 300 ml tetrahydrofuran were added under nitrogen, the mixture was cooled to −10-−15° C., 78 ml (0.16 mol, 2 mol/L) solution of lithium diisopropylamide in n-heptane was added dropwise for about 30 min, after the addition was complete, the reaction was kept at this temperature for 30 min, 4.8 ml (0.077 mol) iodomethane was added dropwise, after the addition was complete, the mixture was warmed to room temperature and stirred for 2 h, 600 ml ethyl acetate and 300 ml water were added, extracted, the organic layer was collected, dried over sodium sulfate, filtered, the filtrate was concentrated to dry under reduced pressure, separated by column chromatography, and 14.5 g compound XIII was obtained, with yield of 46.7%. 1H NMR (CDCl3): δ 1.07-1.21 (m, 2H), 1.41 (d, 3H, J=6.7 Hz), 1.45 (s, 10H), 1.55 (q, 2H, J=7.4 Hz), 1.66-1.69 (m, 1H), 1.80-1.83 (m, 1H), 2.64-2.71 (m, 2H), 3.17-3.24 (m, 1H), 3.92-4.00 (m, 1H), 4.06-4.09 (m, 2H), 4.41 (q, 1H, J=6.7 Hz), 6.05 (s, 2H), 6.82 (s, 1H), 7.20 (s, 1H); MS (ESI): m/z 403 [M+H]+.

Workup

  1. additionafter the addition
  2. additionafter the addition
  3. temperaturethe mixture was warmed to room temperature
  4. extractionextracted
  5. customthe organic layer was collected
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customto dry under reduced pressure
  10. customseparated by column chromatography

Sources & evidence

ORD record
ord-db180895aa5442dabbf10de301422f57
Source dataset
uspto-grants-2016_05
Patent number
US09346818B2

Reaction notes

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