2-Chloroethyl methyl ether → HCID 68993968, compound

HRID 216086Notes

Reaction equation

HRID 216086 reaction equation
[OH:1][C:2]1([C:15]([O:17][CH3:18])=[O:16])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].Cl[CH2:22][CH2:23][O:24][CH3:25]>CN(C=O)C>[CH3:25][O:24][CH2:23][CH2:22][O:1][C:2]1([C:15]([O:17][CH3:18])=[O:16])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 533992151-tert-Butyl 4-methyl 4-hydroxypiperidine-1,4-dicarboxylate

Product 1

HCID 68993968HCID 68993968, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-tert-butyl 4-methyl 4-hydroxypiperidine-1,4-dicarboxylate (360 mg, 1.39 mmol) in DMF (5.6 mL) was carefully added sodium hydride (60% dispersion in mineral oil, 84 mg, 2.08 mmol). The mixture was stirred for 30 minutes at room temperature. 1-Chloro-2-methoxyethane (0.38 mL, 4.17 mmol) was added, and the reaction was stirred at 60° C. for 72 hours. The reaction was quenched with 25 mL of water. The aqueous layer was extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine, dried with MgSO4, and concentrated under vacuum. Silica gel chromatography (20-35% ethyl acetate:hexanes) provided the title compound and starting material as a mixture that was carried forward (150 mg, 1:2 product:starting material).

Workup

  1. stirringthe reaction was stirred at 60° C. for 72 hours
  2. customThe reaction was quenched with 25 mL of water
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×25 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7225012dcc3f4865ad2e74e4f9e0d913
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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