Methyl iodide → HCID 54496807, compound

HRID 564719Notes

Reaction equation

HRID 564719 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[CH3:6][O:7][C:8]1([C:17]2[O:27][C:20]3=[C:21]([O:25][CH3:26])[N:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)[CH2:13][CH2:12][N:11]([C:14](O)=[O:15])[CH2:10][CH2:9]1.[H-].[Na+].IC>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:14]([N:11]1[CH2:10][CH2:9][C:8]([O:7][CH3:6])([C:17]2[O:27][C:20]3=[C:21]([O:25][CH3:26])[N:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)[CH2:13][CH2:12]1)=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69960434HCID 69960434, compound

Product 1

HCID 54496807HCID 54496807, compoundYield 124.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-methoxy-4-(7-methoxyfuro[2,3-c]pyridin-2-yl)piperidine carboxylic acid tert-butyl alcohol (8.59 g) in dry N,N-dimethylformamide (100 ml) was stirred at room temperature under an atmosphere of dry nitrogen. Sodium hydride (60% in oil, 1.18 g) was added portionwise and stirring continued for 30 minutes. Iodomethane (3.07 ml) was added and stirring continued for 80 minutes. The mixture was diluted with ethyl acetate (300 ml) and washed with water (4×100 ml) and brine (1×100 ml). The organic extract was dried over magnesium sulphate, filtered and the solvent removed in vacuo to give the title compound (10.19 g) as a pale yellow liquid.

Workup

  1. stirringstirring
  2. waitcontinued for 80 minutes
  3. washwashed with water (4×100 ml) and brine (1×100 ml)
  4. extractionThe organic extract
  5. dry with materialwas dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a0059d29a890413f8a3a58c75e9f5614
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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