Chloromethyl Methyl Ether → HCID 67374757, compound

HRID 1971953Notes

Reaction equation

HRID 1971953 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1)=[O:4].CCN(C(C)C)C(C)C.[CH3:28][O:29][CH2:30]Cl>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH2:6][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:9][C:10]=1[O:11][CH2:28][O:29][CH3:30])=[O:4]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 112768931-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate

Product 1

HCID 67374757HCID 67374757, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butylester 3-methyl ester (10 mmol, 2.71 g) and DIEA (1 mL) in DCM was added methoxymethyl chloride (1.3 mL) drop-wise and continued stirring for 16 h at room temperature. Volatiles were removed under reduced pressure, the resultant residue was taken up in ethyl acetate (50 mL), washed with water (25 mL), dried the organic layer, filtered and concentrated under reduced pressure. The resultant residue was purified by flash column chromatography using mixture of hexanes and ethyl acetate to provide 4-methoxymethoxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester.

Workup

  1. customVolatiles were removed under reduced pressure
  2. washwashed with water (25 mL)
  3. customdried the organic layer
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant residue was purified by flash column chromatography
  7. additionmixture of hexanes and ethyl acetate

Sources & evidence

ORD record
ord-35ab47fe3acb405b8d788ce57c73f830
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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