Chloride → HCID 49806450, compound

HRID 2381211Notes

Reaction equation

HRID 2381211 reaction equation
Cl[CH:2]1[NH+:11]2[CH2:12][CH2:13][C:14]3[C:19]([C:10]2=[CH:9][C:8]2[CH:7]=[CH:6][C:5]([O:23][CH3:24])=[C:4]([O:25][CH3:26])[C:3]1=2)=[CH:18][C:17]1[O:20][CH2:21][O:22][C:16]=1[CH:15]=3.[Cl-]>O1CCCC1>[CH3:26][O:25][C:4]1[C:3]2[C:2]3([CH2:7][CH2:8][CH2:3][CH2:2]3)[N:11]3[CH2:12][CH2:13][C:14]4[C:19]([C:10]3=[CH:9][C:8]=2[CH:7]=[CH:6][C:5]=1[O:23][CH3:24])=[CH:18][C:17]1[O:20][CH2:21][O:22][C:16]=1[CH:15]=4

Participants

4

Reactant 2

HCID 312ChlorideHCID 86647495HCID 86647495, compound

Product 1

HCID 49806450HCID 49806450, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 8-chloro-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; chloride (1.34 g, 3.3 mmol) in anhydrous tetrahydrofuran (100 mL) at 0° C. was added butyl-1,4-dimagnesium bromide solution (3 M in tetrahydrofuran, 17.4 mL, 4.95 mmol) dropwise. After stirring at 0° C. for 30 min, the reaction was quenched by adding saturated aqueous ammonium chloride solution (30 mL). The mixture was extracted with diethyl ether (2×100 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was re-crystallized from methanol to afford 9′,10′-dimethoxy-5′,6′-dihydrospiro[cyclopentane-1,8′-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline] (120 mg, 10%). LC/MS m/e calcd for C24H25NO4 (M+H)+: 392.47, observed: 392.2; 1H NMR (400 MHz, Chloroform-d) δ ppm 1.84-1.97 (m, 2 H) 1.97-2.09 (m, 2 H) 2.18-2.30 (m, 2 H) 2.37-2.49 (m, 2 H) 2.82 (t, J=5.56 Hz, 2 H) 3.31 (t, J=5.56 Hz, 2 H) 3.85 (s, 3 H) 3.88 (s, 3 H) 5.73 (s, 1 H) 5.95 (s, 2 H) 6.58 (s, 1 H) 6.64 (d, J=8.34 Hz, 1 H) 6.75 (d, J=8.34 Hz, 1 H) 7.16 (s, 1 H).

Workup

  1. customthe reaction was quenched
  2. additionby adding saturated aqueous ammonium chloride solution (30 mL)
  3. extractionThe mixture was extracted with diethyl ether (2×100 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was re-crystallized from methanol

Sources & evidence

ORD record
ord-388045a23e594ff7bf91ca6930369b23
Source dataset
uspto-grants-2012_09
Patent number
US08258149B2

Reaction notes

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