Sodium borohydride → HCID 49806333, compound

HRID 2381213Notes

Reaction equation

HRID 2381213 reaction equation
[CH3:1][O:2][C:3]1[C:23]2[C:22]([CH3:25])([CH3:24])[N:10]3[CH2:11][CH2:12][C:13]4[C:18]([C:9]3=[C:8]([CH3:26])[C:7]=2[CH:6]=[CH:5][C:4]=1[O:27][CH3:28])=[CH:17][C:16]1[O:19][CH2:20][O:21][C:15]=1[CH:14]=4.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:23]2[C:22]([CH3:25])([CH3:24])[N:10]3[CH2:11][CH2:12][C:13]4[C:18]([CH:9]3[CH:8]([CH3:26])[C:7]=2[CH:6]=[CH:5][C:4]=1[O:27][CH3:28])=[CH:17][C:16]1[O:19][CH2:20][O:21][C:15]=1[CH:14]=4

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 49806215HCID 49806215, compound

Product 1

HCID 49806333HCID 49806333, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 9,10-dimethoxy-8,8,13-trimethyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (60 mg, 0.16 mmol) in methanol (10 mL) was added sodium borohydride (15 mg, 0.39 mmol) in small portions at 0° C. After stirring at 0° C. for 1 h, the reaction solvent was concentracted (? 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. The residue was re-crystallized from methanol to afford 9,10-dimethoxy-8,8,13-trimethyl-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (30 mg, 49%). LC/MS m/e calcd for C23H27NO4 (M+H)+: 382.48, observed: 382.2; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.78 (d, J=6.82 Hz, 3 H) 1.41 (s, 3 H) 1.57 (s, 3 H) 2.31-2.40 (m, 1 H) 2.55-2.62 (m, 1 H) 2.66-2.75 (m, 1 H) 2.94-3.02 (m, 1 H) 3.23-3.30 (m, 1 H) 3.79 (d, J=6.06 Hz, 6 H) 4.03 (s, 1 H) 5.95 (d, J=3.28 Hz, 2 H) 6.66 (s, 1 H) 6.81 (m, 2 H) 6.93 (d, J=8.59 Hz, 1 H).

Workup

  1. concentration(? 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
  6. customThe residue was re-crystallized from methanol

Sources & evidence

ORD record
ord-5711eda5fa7d49249cb31e638ce9d695
Source dataset
uspto-grants-2012_09
Patent number
US08258149B2

Reaction notes

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