ChemicalBook CAS DataBase List 3-(Trifluoromethyl)benzylamine

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 Synthesis

402-23-3
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227616-77-5 Synthesis

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

227616-77-5
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2740-83-2
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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
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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