Bromide ion → HCID 49806335, compound

HRID 2381215Notes

Reaction equation

HRID 2381215 reaction equation
[CH3:1][O:2][C:3]1[C:23]2[C:22]([CH3:25])([CH3:24])[NH+:10]3[CH2:11][CH2:12][C:13]4[C:18]([CH:9]3[CH:8]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[C:7]=2[CH:6]=[CH:5][C:4]=1[O:33][CH3:34])=[CH:17][C:16]1[O:19][CH2:20][O:21][C:15]=1[CH:14]=4.[Br-].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:23]2[C:22]([CH3:24])([CH3:25])[N:10]3[CH2:11][CH2:12][C:13]4[C:18]([CH:9]3[CH:8]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[C:7]=2[CH:6]=[CH:5][C:4]=1[O:33][CH3:34])=[CH:17][C:16]1[O:19][CH2:20][O:21][C:15]=1[CH:14]=4

Participants

5

Reactant 3

HCID 259Bromide ionHCID 4311764Sodium borohydrideHCID 86647497HCID 86647497, compound

Product 1

HCID 49806335HCID 49806335, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 9,10-dimethoxy-8,8-dimethyl-13-pyridin-2-ylmethyl-5,6,8,13-tetrahydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; bromide (64 mg, 0.12 mmol) in methanol (10 mL) was added sodium borohydride (9 mg, 0.24 mmol) in small portions at 25° C. After stirring at 25° C. for 20 min, the mixture was concentrated in vacuo. The resulting residue was extracted with diethyl ether (2×50 mL), washed with water (2×25 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 9,10-dimethoxy-8,8-dimethyl-13-pyridin-2-ylmethyl-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (12 mg, 21%). LC/MS m/e calcd for C28H30N2O4 (M+H)+: 459.56, observed: 459.3; 1H NMR (400 MHz, MeOD) δ ppm 1.87 (s, 3 H) 2.03 (s, 3 H) 3.00-3.09 (m, 2 H) 3.25-3.30 (m, 1 H) 3.55 (m, 1 H) 3.82 (s, 3 H) 3.89 (s, 3 H) 4.22 (t, J=5.68 Hz, 1 H) 4.26-4.33 (m, 1 H) 5.20 (d, J=5.05 Hz, 1 H) 6.01 (d, J=4.04 Hz, 2 H) 6.75 (s, 1 H) 6.98 (s, 1 H) 7.01-7.04 (m, 2 H) 7.18 (d, J=8.59 Hz, 1 H) 7.24-7.30 (m, 1 H) 7.73 (t, J=7.71 Hz, 1 H) 8.48 (d, J=5.05 Hz, 1 H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. extractionThe resulting residue was extracted with diethyl ether (2×50 mL)
  3. washwashed with water (2×25 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4de9da214b1e4f96bde703fca5b3f053
Source dataset
uspto-grants-2012_09
Patent number
US08258149B2

Reaction notes

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