Chloromethyl Methyl Ether → HCID 59438435, compound

HRID 2177485Notes

Reaction equation

HRID 2177485 reaction equation
[OH:1][CH:2]1[CH2:7][C:6]([N+:14]([O-:16])=[O:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][N:4]([CH3:17])[C:3]1=[O:18].C(N(C(C)C)C(C)C)C.[CH3:28][O:29][CH2:30]Cl>COCCOC>[CH3:28][O:29][CH2:30][O:1][CH:2]1[CH2:7][C:6]([N+:14]([O-:16])=[O:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][N:4]([CH3:17])[C:3]1=[O:18]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl Ether2×HCID 81531Diisopropylethylamine2×HCID 59438453HCID 59438453, compound

Product 1

HCID 59438435HCID 59438435, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 50 mg (0.2 mmol) rac-3-hydroxy-1-methyl-5-nitro-5-phenyl-piperidin-2-one and 52 ul (0.3 mmol) N-ethyl diisopropylamine in 1,2-dimethoxyethane were added 23 ul (0.3 mmol) chloromethyl methyl ether at room temperature. After 1 hour, the solution was heated in a 60° C. oil bath for 20 hours. The mixture was cooled to room temperature. 52 ul (0.3 mmol) N-ethyl diisopropylamine and 23 ul (0.3 mmol) chloromethyl methyl ether were added. The mixture was heated in a 60° C. oil bath for 4 hours. The solvent was removed in vacuo. The residue was taken in ethyl acetate. The mixture was washed once with water. The aqueous layer was extracted once with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 30 mg (51%) of the title compound as a yellow oil. MS (m/e): 295.2 (MH+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. temperatureThe mixture was heated in a 60° C. oil bath for 4 hours
  3. customThe solvent was removed in vacuo
  4. washThe mixture was washed once with water
  5. extractionThe aqueous layer was extracted once with ethyl acetate
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%)

Sources & evidence

ORD record
ord-f9c155b573924dc9ae11c7db83aaa56e
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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