Sodium borohydride → HCID 59574875, compound

HRID 2381217Notes

Reaction equation

HRID 2381217 reaction equation
[CH2:1]([C:4]1([CH2:29][CH:30]=[CH2:31])[N:13]2[CH2:14][CH2:15][C:16]3[C:21]([C:12]2=[CH:11][C:10]2[CH:9]=[CH:8][C:7]([O:25][CH3:26])=[C:6]([O:27][CH3:28])[C:5]1=2)=[CH:20][C:19]1[O:22][CH2:23][O:24][C:18]=1[CH:17]=3)[CH:2]=[CH2:3].[BH4-].[Na+]>CO>[CH2:29]([C:4]1([CH2:1][CH:2]=[CH2:3])[N:13]2[CH2:14][CH2:15][C:16]3[C:21]([CH:12]2[CH2:11][C:10]2[CH:9]=[CH:8][C:7]([O:25][CH3:26])=[C:6]([O:27][CH3:28])[C:5]1=2)=[CH:20][C:19]1[O:22][CH2:23][O:24][C:18]=1[CH:17]=3)[CH:30]=[CH2:31]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 49806218HCID 49806218, compound

Product 1

HCID 59574875HCID 59574875, compoundYield 64,177%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 8,8-diallyl-9,10-dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (110 mg, 0.26 mmol) in methanol (20 mL) was added sodium borohydride (10 mg, 0.26 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 8,8-diallyl-9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (70 g, 64%). LC/MS m/e calcd for C26H29NO4 (M+H)+: 420.53, observed: 420.3; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.32-2.44 (m, 2 H) 2.54-2.64 (m, 1 H) 2.64-2.75 (m, 3 H) 2.90 (s, 2 H) 3.02-3.12 (m, 2 H) 3.80 (d, J=2.78 Hz, 6 H) 4.30 (d, J=2.02 Hz, 1 H) 4.69 (d, J=10.36 Hz, 1 H) 4.74-4.88 (m, 2 H) 5.01 (d, J=16.93 Hz, 1 H) 5.36-5.48 (m, 1 H) 5.58-5.72 (m, 1 H) 5.93 (s, 2 H) 6.63 (s, 1 H) 6.78-6.85 (m, 2 H) 6.94 (d, J=8.59 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-b1eebcaedf5b4e468dcbce22431a8941
Source dataset
uspto-grants-2012_09
Patent number
US08258149B2

Reaction notes

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