Methyl iodide → HCID 68544973, compound

HRID 1443063Notes

Reaction equation

HRID 1443063 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH:14]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:28][OH:29])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:32]I>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH:14]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:28][O:29][CH3:32])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodide3×HCID 24758Sodium hydride3×HCID 68546102HCID 68546102, compound

Product 1

HCID 68544973HCID 68544973, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[(2-Hydroxymethyl-phenoxy)-phenyl-methyl]-morpholine-4-carboxylic acid tert-butyl ester (0.44 g) was taken up in THF (10 mL) and placed in a room temperature bath for the addition of NaH (0.05 g). The mixture was stirred for 10 min, and then MeI (0.17 g) was added and stirred at room temperature for 3 h. The mixture was again treated with NaH and MeI and stirred at room temperature for 48 h. Starting material was still present, so the mixture was treated with NaH. MeI was passed through a plug of basic alumina and then added. After 3 h, the reaction was carefully quenched by the addition of water. The mixture was extracted with ether (3×30 ml), and the organics were combined, washed with brine (1×20 ml), dried over MgSO4, filtered and concentrated. The colorless oil was taken up in DCM and pumped onto silica and then purified by MPLC (Hexane:EtOAc 95:5 to 40:60). Fractions containing the desired product were combined and concentrated to give 0.317 g of Preparation of 2-[(2-Methoxymethyl-phenoxy)-phenyl-methyl]-morpholine-4-carboxylic acid tert-butyl ester (70% yield).

Workup

  1. customplaced in a room temperature
  2. stirringstirred at room temperature for 3 h
  3. stirringstirred at room temperature for 48 h
  4. additionadded
  5. waitAfter 3 h
  6. customthe reaction was carefully quenched by the addition of water
  7. extractionThe mixture was extracted with ether (3×30 ml)
  8. washwashed with brine (1×20 ml)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. custompurified by MPLC (Hexane:EtOAc 95:5 to 40:60)
  13. additionFractions containing the desired product
  14. concentrationconcentrated
  15. customto give

Sources & evidence

ORD record
ord-68327c63c0e84deaacf0e2e1c817c2fb
Source dataset
uspto-grants-2010_02
Patent number
US07659394B2

Reaction notes

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