3-(Trifluoromethyl)benzylamine synthesis

4synthesis methods

Product Name:3-(Trifluoromethyl)benzylamine
CAS Number:2740-83-2
Molecular formula:C8H8F3N
Molecular Weight:175.15

402-23-3

Pyrrolo[1,2-a]pyrimidine-6-carboxylic acid, 4,6,7,8-tetrahydro-4-oxo-3-[[(phenylmethoxy)carbonyl]amino]-, (6S)-

227616-77-5

2740-83-2

Pyrrolo[1,2-a]pyrimidine-6-carboxylic acid, 4,6,7,8-tetrahydro-4-oxo-3-[[(phenylmethoxy)carbonyl][[3-(trifluoromethyl)phenyl]methyl]amino]-, (6S)-

437761-03-0

Synthesis of (6S)-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-A]pyrimidine-6-carboxylic acid from 3-(trifluoromethyl)benzyl bromide and (S)-3-(((benzyloxy)carbonyl)amino)-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine -6-carboxylic acid (12a) was performed in the following general steps: to a mixture of acid 1i (4.50 g, 13.7 mmol) in 70 mL THF at 0 °C was added 3-(trifluoromethyl)benzyl bromide (8.35 mL, 54.7 mmol), NaH (60% dispersed in oil, 1.64 g, 41.4 mmol) and TBAI (100 mg, catalytic amount). The reaction mixture was stirred at room temperature for 15 h. The reaction was then quenched by the addition of 50 mL of H2O. The volatile solvent was removed by rotary evaporation and the resulting aqueous solution was partitioned with Et2O. The organic phase was extracted with 20% saturated NaHCO3 solution (3 times). The combined organic extracts were acidified with 1N HCl and extracted with EtOAc (5 times). The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated to give 6.18 g (93% yield) of 3-(trifluoromethyl)benzylamine (12a), a product that could be used in the next step without further purification.

402-23-3 Synthesis

402-23-3
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227616-77-5 Synthesis

227616-77-5
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2740-83-2
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437761-03-0
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Yield:2740-83-2 6.18g (93%)

Reaction Conditions:

with NaH;tetra-(n-butyl)ammonium iodide in tetrahydrofuran;water;

Steps:

12 (6S)-3-{[(Benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid (12a)

(6S)-3-{[(Benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid (12a) To a mixture of acid 1i (4.50 g, 13.7 mmol) in 70 mL THF at 0° C., was added 3-(trifluoromethyl)benzyl bromide (8.35 mL, 54.7 mmol), NaH (60% dispersion in oil, 1.64 g, 41.4 mmol), and TBAI (100 mg, catalytic). The reaction was stirred at rt for 15 h, then quenched with the addition of 50 mL H₂O. The volatile solvents were removed by rotary evaporation and the aqueous solution obtained was partitioned with Et₂O. The organic phase was extracted with 20% sat. NaHCO₃ (3*). The combined organic extract was acidified with 1N HCl and extracted with EtOAc (5*). The combined organic extract was washed (brine), dried (Na₂SO₄), and concentrated to afford 6.18g (93%) of the 3-(trifluoromethyl)benzyl amine (12a), which was used in the following step without additional purification.

References:

US2003/64962,2003,A1