Water → HCID 18364774, compound

HRID 380524Notes

Reaction equation

HRID 380524 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([OH:23])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24]I.[H-].[Na+].O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([O:23][CH3:24])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18364805HCID 18364805, compound

Product 1

HCID 18364774HCID 18364774, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.218 g (0.68 mmol) of 1-t-butoxy carbonyl-4-(3-phenyl-1-hydroxypropyl)piperidine (Example 239) and 0.3 mL of methyl iodide in 2 mL of DMF was added 0.066 g (1.5 mmol)of NaH (60% dispersion in mineral oil) and the mixture was stirred for 16 h at rt. To the reaction was added 5 mL of water and the mixture was extracted with ethyl acetate. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 4:1) to give 1-t-butoxy carbonyl-4-(3-phenyl-1-(RS)-methoxypropyl)piperidine. Removal of the BOC protecting group was achieved as described in Example 233, Step 6 to give the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic fractions were washed with sat'd NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-adc01bf3608a43d08fdbf5053d02ccb3
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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