反应 #1563919

反应方程式

carbon monoxide

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

CH3CN

triethylamine

→

title compound

收率 143.2%

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

收率 143.2%

溶剂

CH3OH

反应条件

后处理

1. 1
   其他Seal the vessel
2. 2
   其他transfer to a round-bottomed flask
3. 3
   洗涤rinsing with CH3OH
4. 4
   浓缩Concentrate the mixture under reduced pressure
5. 5
   其他to furnish an orange residue
6. 6
   萃取Add water (50 mL), then extract with EtOAc (2×50 mL)
7. 7
   洗涤Wash the combined organic phases with saturated aqueous NaCl (25 mL)
8. 8
   其他separate the layers
9. 9
   干燥dry the organic phase over MgSO4
10. 10
    过滤filter
11. 11
    其他to remove the solids
12. 12
    浓缩concentrate the filtrate under reduced pressure
13. 13
    其他to give crude product
14. 14
    其他Purify the product by flash chromatography on silica gel eluting with a gradient of 0% to 60% EtOAc/hexanes
15. 15
    浓缩Concentrate the fractions
16. 16
    workup.ADDITIONcontaining the desired product under reduced pressure

实验过程

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).

来源