Sodium borohydride → HCID 58266768, compound

HRID 1888473Notes

Reaction equation

HRID 1888473 reaction equation
[BH4-].[Na+].[I-].[CH2:4]([N+:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:18][CH3:19])[CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[CH:7]=1)[CH3:5]>CO>[CH2:4]([N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:18][CH3:19])[CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[CH2:7]1)[CH3:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67027655HCID 67027655, compound

Product 1

HCID 58266768HCID 58266768, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (260 mg, 6.86 mmol) was added to a cooled (0° C.) solution of 2-ethyl-6,8-dimethoxy-3,4-dihydroisoquinolinium iodide (1.19 g, 3.43 mmol) in methanol (15 mL). On complete addition the mixture was allowed to warm to ambient temperature and stirred for 1.5 h. The mixture was evaporated in vacuo and the resultant residue was partitioned between diethyl ether and water. The organic phase was dried over sodium sulfate, filtered and evaporated to afford the title compound as a yellow oil (741 mg, 98%). 1H NMR (CDCl3, 300 MHz): 6.27 (d, J=2.3 Hz, 1H), 6.24 (d, J=2.3 Hz, 1H), 3.78 (s, 3H), 3.76 (s, 3H), 3.51-3.47 (m, 2H), 2.89-2.83 (m, 2H), 2.71-2.64 (m, 2H), 2.60 (q, J=7.2 Hz, 2H), 1.19 (t, J=7.2 Hz, 3H). LCMS (Method B): RT=1.62 min, M+H+=222.

Workup

  1. additionOn complete addition the mixture
  2. customThe mixture was evaporated in vacuo
  3. customthe resultant residue was partitioned between diethyl ether and water
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f97ccc40a6fb4df093cdf6f08f0e8ff9
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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