Methyl iodide → HCID 89814182, compound

HRID 715119Notes

Reaction equation

HRID 715119 reaction equation
[CH2:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:9][CH2:10][CH2:11][C:12]([CH3:15])([OH:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23]I>C1COCC1>[CH2:1]([N:8]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:23])([CH3:15])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86222790HCID 86222790, compound

Product 1

HCID 89814182HCID 89814182, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Treat a 0° C. solution of 5-(dibenzylamino)-2-methylpentan-2-ol (3 g, 10.2 mmol) in THF (25 mL), under N2, portion-wise with KH (30%, 1.5 g, 11.3 mmol), stir at 0° C. for 0.5 h, add MeI (1.6 g, 11.3 mmol) drop-wise, warm to RT and stir for 3 h. Cool to 0° C., quench with satd. NH4Cl, partially concentrate under reduced pressure, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate and purify via silica gel chromatography to afford the title compound (3.1 g, 97%). 1H NMR (400 MHz, DMSO-d6): δ 7.38-7.21 (m, 10H), 3.57 (s, 4H), 3.14 (s, 3H), 2.42 (t, J=7.2 Hz, 2H), 1.58-1.52 (m, 2H), 1.43-1.39 (m, 2H), 1.11 (s, 6H).

Workup

  1. temperaturewarm to RT
  2. stirringstir for 3 h
  3. temperatureCool to 0° C.
  4. customquench with satd
  5. concentrationNH4Cl, partially concentrate under reduced pressure
  6. extractionextract with EtOAc (3×)
  7. washwash the combined organics with brine
  8. dry with materialdry over Na2SO4
  9. concentrationconcentrate
  10. custompurify via silica gel chromatography

Sources & evidence

ORD record
ord-facbf23521ab48398bfaa79db0263fa0
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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