Formaldehyde → HCID 12303970, compound

HRID 1757599Notes

Reaction equation

HRID 1757599 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([OH:15])[C:12]=1[O:13][CH3:14])[CH:9]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[NH:8][CH2:7][CH2:6]2.[CH2:25]=O.[BH4-].[Na+]>C(Cl)(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([OH:15])[C:12]=1[O:13][CH3:14])[CH:9]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)[N:8]([CH3:25])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 9818855HCID 9818855, compound

Product 1

HCID 12303970HCID 12303970, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

6,7-Dimethoxy-1-(4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-8-ol (2.55 g, 7.74 mmol) obtained in Example 1-2 was dissolved in 100 ml of chloroform-methanol (1:1), 35% formalin (3.6 ml, 45.3 mmol) was added and the mixture was stirred at room temperature for 2 hours. Sodium borohydride (3.40 g, 89.8 mmol) was added under ice cooling and the mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, 200 ml of water was added to the resultantresidue, and the mixture was neutralized with 1N hydrochloric acid and thenextracted with chloroform (100 ml×3). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol) to give 2.09 g (yield: 79%) of the captioned compound as pale yellow powder. Melting point: 112°-114° C. FAB-MS (m/z, (C20H25NO4 +H)+ ): 344 1H-NMR (300MHz, CDCl3, δ ppm): 2.35 (3H, s), 2.35-2.45 (1H, m), 2.73-2.87 (2H, m), 2.98 (1H, dd, J=3.2Hz, 14.2Hz), 3.20-3.32 (1H, m), 3.78(3H, s), 3.83 (3H, s), 3.88 (3H, s), 3.95 (1H, d, J=3.2Hz, 8.8Hz), 6.20 (1H, s), 6.80 (1H, d, J=8.8Hz), 7.18 (1H, d, J=8.8Hz)

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customThe solvent was removed under reduced pressure, 200 ml of water
  3. additionwas added to the resultantresidue
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-b3a3769f978c4f3e9ac78b58bc851ce9
Source dataset
uspto-grants-1995_08
Patent number
US05446164

Reaction notes

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