Hydrochloric Acid → HCID 86686025, compound

HRID 2277730Notes

Reaction equation

HRID 2277730 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:12]1[C:21]3[CH2:20][CH2:19][CH2:18][C:17]4(OCC(C)(C)C[O:22]4)[C:16]=3[CH:15]=[N:14][CH:13]=1)[C:5]2([CH3:30])[CH3:29].Cl.O1CCOCC1>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8]([C:7](=[O:11])[N:6]([C:12]3[C:21]4[CH2:20][CH2:19][CH2:18][C:17](=[O:22])[C:16]=4[CH:15]=[N:14][CH:13]=3)[C:5]2([CH3:30])[CH3:29])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86686026HCID 86686026, compound

Product 1

HCID 86686025HCID 86686025, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-chloro-2-(5,5-dimethyl-6′,7′-dihydro-5′H-spiro[1,3-dioxane-2,8′-isoquinolin]-4′-yl)-3,3-dimethyl-2,3-dihydro-1H-isoindol-1-one (0.66 g, 1.55 mmol) in MeOH (2 mL) was added 4 N HCl in dioxane (1.5 mL, 6 mmol) and the reaction mixture was stirred at room temperature for 2 hours. After evaporation of the solvent, the residue was diluted with DCM (20 mL) and washed with satd. aq. NaHCO3 (10 mL) solution. The organic layer was dried over anhy. Na2SO4, filtered and evaporated to dryness. The residue obtained was purified by silica gel flash chromatography eluting with a 0 to 50% hexane-ethyl acetate gradient to give the title compound (421 mg, 80%) as a light yellow solid. MS: 341.1 (M+H+).

Workup

  1. customAfter evaporation of the solvent
  2. additionthe residue was diluted with DCM (20 mL)
  3. washwashed with satd
  4. customThe organic layer was dried over anhy
  5. filtrationNa2SO4, filtered
  6. customevaporated to dryness
  7. customThe residue obtained
  8. customwas purified by silica gel flash chromatography
  9. washeluting with a 0 to 50% hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-56a234cc1d944eab988975c363de4c71
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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