Ethyl N-Boc-(indol-3-yl)acetate/tert-butyl 3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate synthesis
- Product Name:Ethyl N-Boc-(indol-3-yl)acetate/tert-butyl 3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate
- CAS Number:786647-50-5
- Molecular formula:C17H21NO4
- Molecular Weight:303.35
Yield:786647-50-5 99%
Reaction Conditions:
with triethylamine;dmap in tetrahydrofuran at 20; for 16 h;
Steps:
Ethyl 1H-indol-3-ylacetate (2 5 g, 12.3 MMOL) was dissolved in THF (60 mL) and to the resulting solution was added Di-tert-butyl carbonate (2. 9 g, 16. 6 MMOL), ET3N (1. 89 mL), and DMAP (150 mg, 1. 23 MMOL). The reaction was stirred for 16 h at rt. The solvent was removed under vacuum and the residue was re-dissolved in ET20 and saturated NAHC03 was added and the mixture was stirred vigorously for 30 min. The organic phase was collected, and dried over NA2SO4. The solvent was removed by vacuum. The crude product was purified further by passing it through a plug of silica using ET20 as eluent. The solvent was removed under vacuum to give ter-butyl 3-(2-ETHOXY-2-OXOETHYL)-1H-INDOLE-1- carboxylate as an oil (3. 73 g, 99%) :'H NMR (CDC13) 8 8. 14 (m, 1H), 7. 54 (m, 2H), 7. 32 (m, 1 H), 7. 24 (m, 2H), 4. 19 (q, 2H), 3. 71 (s, 1H), 1. 68 (s, 9H), 1. 29 (t, 3H).
References:
WO2004/94376,2004,A1 Location in patent:Page 203-204
87-51-4
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