반응 #1563919

반응 방정식

carbon monoxide

(S)—N-tert-butoxycarbonyl-1-(4-bromophenyl)ethylamine

CH3CN

triethylamine

→

title compound

수율 143.2%

methyl (S)-4-(1-tert-butoxycarbonylaminoethyl)benzoate

수율 143.2%

용매

CH3OH

반응 조건

후처리

1. 1
   기타Seal the vessel
2. 2
   기타transfer to a round-bottomed flask
3. 3
   세척rinsing with CH3OH
4. 4
   농축Concentrate the mixture under reduced pressure
5. 5
   기타to furnish an orange residue
6. 6
   추출Add water (50 mL), then extract with EtOAc (2×50 mL)
7. 7
   세척Wash the combined organic phases with saturated aqueous NaCl (25 mL)
8. 8
   기타separate the layers
9. 9
   건조dry the organic phase over MgSO4
10. 10
    여과filter
11. 11
    기타to remove the solids
12. 12
    농축concentrate the filtrate under reduced pressure
13. 13
    기타to give crude product
14. 14
    기타Purify the product by flash chromatography on silica gel eluting with a gradient of 0% to 60% EtOAc/hexanes
15. 15
    농축Concentrate the fractions
16. 16
    workup.ADDITIONcontaining the desired product under reduced pressure

실험 절차

To a Parr autoclave with mechanical stirring, add Pd(OAc)2 (120 mg, 0.53 mmol), 1,1′-bis(diphenylphosphino)ferrocene (355 mg, 0.64 mmol), (S)—N-tert-butoxycarbonyl-1-(4-bromophenyl)ethylamine (1.50 g, 5.0 mmol), anhydrous CH3CN (45 mL), anhydrous CH3OH (30 mL), and triethylamine (1.9 mL, 13.63 mmol). Seal the vessel and pressurize with carbon monoxide to 724 kPag. Heat the vessel to 85° C. and stir the mixture overnight. Vent the reaction vessel (Caution—poison gas!) and transfer to a round-bottomed flask, rinsing with CH3OH. Concentrate the mixture under reduced pressure to furnish an orange residue. Add water (50 mL), then extract with EtOAc (2×50 mL). Wash the combined organic phases with saturated aqueous NaCl (25 mL), then separate the layers, dry the organic phase over MgSO4, filter to remove the solids, and concentrate the filtrate under reduced pressure to give crude product. Purify the product by flash chromatography on silica gel eluting with a gradient of 0% to 60% EtOAc/hexanes. Concentrate the fractions containing the desired product under reduced pressure to furnish the title compound as a white solid (1.00 g, 72% yield). Mass spectrum (m/z) 224 (M+2H−t-Bu)+, 302 (M+Na)+, 581 (2M+Na)+. 1H NMR (400 MHz, DMSO-d6): δ 7.89 (d, =8.4 Hz, 2H), 7.41 (d, J=8.2 Hz, 2H), 4.64 (dq, J=7.4, 6.8 Hz, 1H), 3.82 (s, 3H), 1.34 (br s, 9H), 1.28 (d, J=7.2 Hz, 3H).

출처