Hydrochloric Acid → HCID 57482555, compound

HRID 1907379Notes

Reaction equation

HRID 1907379 reaction equation
Cl.C1COCC1.[CH3:7][O:8][C:9]1[C:18]2[O:17]C(C)(C)[O:15][CH2:14][C:13]=2[CH:12]=[C:11]([N:21]2[CH2:25][CH2:24][CH2:23][C:22]2=[O:26])[CH:10]=1>O>[OH:17][C:18]1[C:9]([O:8][CH3:7])=[CH:10][C:11]([N:21]2[CH2:25][CH2:24][CH2:23][C:22]2=[O:26])=[CH:12][C:13]=1[CH2:14][OH:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 66645997HCID 66645997, compound

Product 1

HCID 57482555HCID 57482555, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10% hydrochloric acid (4 ml) was added to a THF solution (7 ml) of 1-(8-methoxy-2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)pyrrolidin-2-one (0.36 g, 1.3 mmol) and the mixture was stirred at room temperature for 17 hours. Water was added to the reaction solution, which was then extracted with dichloromethane. The extracted material was dried over magnesium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography (dichloromethane:methanol:=300:1→30:1). The purified product was concentrated to dryness under reduced pressure to obtain 1-(4-hydroxy-3-hydroxymethyl-5-methoxyphenyl)pyrrolidin-2-one (0.31 g) as light brown powder.

Workup

  1. extractionwas then extracted with dichloromethane
  2. dry with materialThe extracted material was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by silica gel column chromatography (dichloromethane:methanol:=300:1→30:1)
  5. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b6c0d816a3b940439bcc4f8d4656b339
Source dataset
uspto-grants-2013_12
Patent number
US08598162B2

Reaction notes

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