Methyl iodide → HCID 9819672, compound

HRID 397217Notes

Reaction equation

HRID 397217 reaction equation
[CH2:1]([C@H:4]1[C:13]2=[C:14]3[C:19](=[CH:20][CH:21]=[C:12]2[C:11]2[C:10]([OH:25])=[CH:9][CH:8]=[CH:7][C:6]=2[O:5]1)[NH:18][C:17]([CH3:23])([CH3:22])[CH:16]=[C:15]3[CH3:24])[CH:2]=[CH2:3].[C:26](O[K])(C)(C)C.IC.[NH4+].[Cl-]>C1COCC1.CC(OC)(C)C>[CH2:1]([C@H:4]1[C:13]2=[C:14]3[C:19](=[CH:20][CH:21]=[C:12]2[C:11]2[C:10]([O:25][CH3:26])=[CH:9][CH:8]=[CH:7][C:6]=2[O:5]1)[NH:18][C:17]([CH3:23])([CH3:22])[CH:16]=[C:15]3[CH3:24])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 12109527HCID 12109527, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 9819672HCID 9819672, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

The product from Example 9 (157 mg) in THF (10 ml) was treated with a 1.0 M solution of tBuOK (1.0 ml) at 0° C. and then treated with iodomethane (0.1 ml). After stirring at room temperature for 2 hours, the mixture was poured into a solution of saturated NH4Cl (15 mL) and stirred briefly before MTBE (15 mL) was added. After stirring for 5 minutes, the organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by column chromatography to give the title compound (134 mg). Anal. calcd for C23H25NO2: C, 79.51; H, 7.25 and N, 4.03; Found: C, 79.26; H, 7.12 and N, 3.80; 1H NMR [(CD3)2SO] δ1.16 (3H, s) 1.17 (3H, s), 2.18 (3H, s), 2.22 (1H, m), 2.46 (1H, m), 3.85 (3H, s), 5.01 (2H, m), 5.44 (1H, br s), 5.77 (1H, dd), 5.82 (1H, M), 6.10 (1H, br s), 6.52 (1H, d), 6.60 (1H, d), 6.70 (1H, d), 7.06 (1H, t) and 7.96 (1H, d); 13CNMR [(CD3)2SO] δ23.8, 28.8, 28.9, 36.5, 49.7, 55.6, 73.4, 105.6, 110.5, 113.4, 113.4, 116.1, 116.4, 127.3, 117.3, 127.3, 127.7, 132.2,133.8, 134.5, 145.8, 151.1, 156.4; APCI-MS: m/z 348 (M+H)+.

Workup

  1. additionwas added
  2. stirringAfter stirring for 5 minutes
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2bc7d166e8f942d2a394a5735d1b7f89
Source dataset
uspto-grants-2003_08
Patent number
US06608216B2

Reaction notes

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