Sodium Methoxide → HCID 69666208, compound

HRID 433986Notes

Reaction equation

HRID 433986 reaction equation
C[O-].[Na+].C([O:7][CH2:8][C@H:9]([N:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:14]=[CH:13]1)[CH2:10][CH3:11])(=O)C>CO>[N:12]1([C@H:9]([CH2:10][CH3:11])[CH2:8][OH:7])[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 69666341HCID 69666341, compound

Product 1

HCID 69666208HCID 69666208, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (163.0 g of 25% in methanol, 1.1 eq.) was added in a single portion to a solution of (2R)-2-(1H-imidazo[4,5-c]quinolin-1-yl)butyl acetate (194.0 g, 1 eq.) in methanol (970 mL). The reaction mixture was stirred at ambient temperature for 3 hours and then concentrated under reduced pressure. The residue was diluted with water (1 L), neutralized (pH 6-7) with acetic acid and then stirred at ambient temperature overnight. The resulting precipitate was isolated by filtration, washed with water (2×200 mL), air dried on the filter and then dried in a vacuum oven overnight at 50° C. to provide 145.5 g of (2R)-2-(1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol as a solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with water (1 L)
  3. stirringstirred at ambient temperature overnight
  4. customThe resulting precipitate was isolated by filtration
  5. washwashed with water (2×200 mL), air
  6. customdried on the
  7. filtrationfilter
  8. customdried in a vacuum oven overnight at 50° C.

Sources & evidence

ORD record
ord-d335ed9437fa432b93ded20c8a3aa991
Source dataset
uspto-grants-2003_12
Patent number
US06670372B2

Reaction notes

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