반응 #11082

반응 방정식

3-(trifluoromethyl)benzyl bromide

NaH

acid 1i

{6-[4-(tert-butoxycarbonylamino-imino-methyl)-benzylcarbamoyl]-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-carbamic acid benzyl ester

THF

→

3-(trifluoromethyl)benzyl amine

수율 93.0%

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

수율 93.0%

반응 조건

후처리

1. 1
   기타quenched with the addition of 50 mL H2O
2. 2
   기타The volatile solvents were removed by rotary evaporation
3. 3
   기타the aqueous solution obtained
4. 4
   기타was partitioned with Et2O
5. 5
   추출The organic phase was extracted with 20% sat. NaHCO3 (3×)
6. 6
   추출The combined aqueous extract
7. 7
   추출extracted with EtOAc (5×)
8. 8
   추출The combined organic extract
9. 9
   세척was washed (brine)
10. 10
    건조dried (Na2SO4)
11. 11
    농축concentrated

실험 절차

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 aqueous extract was acidified with 1N HCl and extracted with EtOAc (5×). The combined organic extract was washed (brine), dried (Na2SO4), and concentrated to afford 6.18 g (93%) of the 3-(trifluoromethyl)benzyl amine (25a), which was used in the following step without additional purification. MS (ESI) 488.3 (M+H+), 510.3 (M+Na+); 486.3 (M−H+).

출처