Triethylamine → HCID 69046637, compound

HRID 2196582Notes

Reaction equation

HRID 2196582 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][NH:10][CH2:11]2)=[O:5].C(N(CC)CC)C.[N:23]1[CH:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[N:23]1[CH:28]=[CH:27][C:26]([CH2:29][N:10]2[CH2:9][CH2:8][C:7]3[C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:11]2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 133894-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 44607840Methyl 1,2,3,4-tetrahydroisoquinoline-5-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 69046637HCID 69046637, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Methoxycarbonyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (1 g, 4.39 mmol) and triethylamine (666 mg, 6.58 mmol) were mostly dissolved in tetrahydrofuran (30 mL). 4-Pyridinecarboxaldehyde (494 mg, 4.61 mmol) and sodium triacetoxyborohydride (1.3 g, 6.15 mmol) were then added to the mixture. The reaction mixture was stirred at room temperature overnight. The reaction was quenched with saturated aqueous sodium bicarbonate. The tetrahydrofuran was removed under vacuum and the remaining residue was dissolved in ethyl acetate then washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over sodium sulfate and concentrated under vacuum to give 1.29 g of methyl 2-(pyridine-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate as a light yellow oil. MS (ESI, pos. ion) m/z: 283.0 (M+1).

Workup

  1. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  2. customThe tetrahydrofuran was removed under vacuum
  3. dissolutionthe remaining residue was dissolved in ethyl acetate
  4. washthen washed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ebf059fe26c546bea9efa902f2f92468
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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