N-T-BOC-PYRROLE
-
N-T-BOC-PYRROLE
structure -
-
CAS No:
5176-27-2
-
Formula:
C9H13NO2
-
Chemical Name:
N-T-BOC-PYRROLE
-
Synonyms:
1-Boc-pyrrole;N-Boc-Pyrrole;N-T-BOC-PYRROLE;N-BOC-1H-PYRROLE;N-Boc-pyrrole 98%;N-T-BOC-PYRROLE-1;tert-butyl-pyrrole-carboxylate;TERT-BUTYL 1-PYRROLECARBOXYLATE;TERT-BUTYL PYRROL-1-CARBOXYLATE;tert-Butylpyrrole-1-carboxylate
-
CAS No:
Safety Information
3
R36/37/38
S26
Xi
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
N-T-BOC-PYRROLE Use and Manufacturing
BocBoc2O (43.65 g, 0.2 mol) and TEA (20.2 g, 0.2 mol)were added to pyrrole (13.42 g, 0.2 mol) in DCM (100 mL)and the resulting mixture was stirred for 2 h at room temperatureand then worked up with DCM (2 x 400 mL) andwater (400 mL). The combined organic layers were driedover MgSO4 and were concentrated to obtain 16 as acolorless oil (31.4 g, yield: 94percent). 1H NMR (600 MHz, CDCl3): 7.27 (s, 2H), 6.25 (s, 2H), 1.62 (s, 9H); 13C NMR(150 MHz, CDCl3): 148.95, 119.98, 111.87, 83.61, 28.01.ESI-MS: m/z 168.4 [M + H]+.Procedure: 70 g (1.04 mol) of pyrrole, 274 g (1.25 mol) of di-t-butyl dicarbonate, 17.6 g (0.1 mol) of 4-dimethylaminopyridine and 1 liter of acetonitrile were added to a 3000 ml single-necked flask , The mixture was stirred at room temperature for 15 hours, and acetonitrile was concentrated to obtain a crude product.The crude product was purified by column chromatography using petroleum ether and ethyl acetate eluent system to give 150 g of 1-tert-butoxycarbonylpyrrole (yield 86percent).Step A: DMAP (1.00 g, 8.2 mmol, 0.14 eq.) was added to a solution of pyrrole (4.00 g, 59 mmol, 1.00 eq.) and(Boc)2O (15.60 g, 71.5 mmol, 1.20 eq.) dissolved in acetonitrile (200 mL). The mixture was stirred at 25°C for 2hours. The mixture was concentrated and the residue was purified by a silica gel column (the eluent is PE) to givet-butyl pyrryl-1-formate (7.80 g, 46.7 mmol, 78.3percent yield) as colorless liquid.The starting material was prepared as follows:
Computed Properties
Molecular Weight:167.20
XLogP3:1.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:167.094628657
Monoisotopic Mass:167.094628657
Topological Polar Surface Area:31.2
Heavy Atom Count:12
Complexity:166
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
