ChemicalBook CAS DataBase List N-T-BOC-PYRROLE

N-T-BOC-PYRROLE synthesis

8synthesis methods

Product Name:N-T-BOC-PYRROLE
CAS Number:5176-27-2
Molecular formula:C9H13NO2
Molecular Weight:167.21

109-97-7

24424-99-5

5176-27-2

General procedure for the synthesis of tert-butyl 1-pyrrolecarboxylate from pyrrole and di-tert-butyl dicarbonate: di-tert-butyl dicarbonate (Boc2O, 9.8 g, 44.7 mmol) and triethylamine (TEA, 6.3 mL, 44.7 mmol) were added sequentially to a solution of pyrrole (3.0 g, 29.8 mmol) in dichloromethane (DCM, 15 mL). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, extraction was performed with dichloromethane (2 x 400 mL) and water (400 mL). The organic layers were combined, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to afford tert-butyl 1-pyrrolecarboxylate (26) as a white solid (7.5 g). Yield: 94%; 1H NMR (300 MHz, CDCl3) δ (ppm): 7.26 (s, 2H), 7.24 (t, J=2.4 Hz, 1H), 6.22 (t, J=2.4 Hz, 1H), 1.60 (d, J=11.7 Hz, 9H); ESI-MS [M+H]+=169.0.

109-97-7 Synthesis

109-97-7
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$9.00/5 g

24424-99-5 Synthesis

24424-99-5
868 suppliers
$13.50/25G

5176-27-2
188 suppliers
$10.00/1g

Yield:5176-27-2 94%

Reaction Conditions:

with triethylamine in dichloromethane at 20; for 2 h;

Steps:

4.1.9. tert-butyl 1H-pyrrole-1-carboxylate (26)
Boc₂O (9.8 g, 44.7 mmol) and TEA (6.3 mL, 44.7 mmol) was added to pyrrole (25) (3.0 g, 29.8 mmol) in DCM (15 mL) and the resulting mixture was stirred for 2h at room temperature and then worked up with DCM (2 × 400 mL) and water (400 mL). The combined organic layers were dried over MgSO₄ and were concentrated to obtain 26 as white solid (7.5 g). Yield: 94%; ¹H NMR (300 MHz, CDCl₃) δ (ppm) 7.26 (s, 2H), 7.24 (t, J = 2.4 Hz, 1H), 6.22 (t, J = 2.4 Hz, 1H), 1.60 (d, J = 11.7 Hz, 9H); ESI [M + H] = 169.0.

References:

You, Hyun;Youn, Hyung-Seop;Im, Isak;Bae, Man-Ho;Lee, Sang-Kook;Ko, Hyojin;Eom, Soo Hyun;Kim, Yong-Chul [European Journal of Medicinal Chemistry,2011,vol. 46,# 4,p. 1153 - 1164] Location in patent:experimental part

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109-97-7 Synthesis

109-97-7
352 suppliers
$9.00/5 g