ChemicalBook CAS DataBase List 6-[7(R)-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthamide

6-[7(R)-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthamide synthesis

11synthesis methods

Product Name:6-[7(R)-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthamide
CAS Number:752243-39-3
Molecular formula:C18H17N3O2
Molecular Weight:307.35

426219-32-1 Synthesis

6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]iMidazol-7-yl)-N-Methyl-2-naphthaMide

426219-32-1
3 suppliers
inquiry

6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide

566939-85-3
81 suppliers
$81.00/5mg

6-[7(R)-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthamide

752243-39-3
16 suppliers
inquiry

Yield:566939-85-3 49% ，752243-39-3 50%

Reaction Conditions:

with Chiralpak AD column in ethanol;hexane;Resolution of racemate;HPLC conditions;optical yield given as %ee;

Steps:

4.29. Optical resolution of 3c using preparative HPLC

Compound 3c (12.8 g, 41.6 mmol) was subjected to optical resolution by preparative HPLC using a Chiralpak AD column (50 mm × 500 mm) using hexane/ethanol (1/1) as an eluent, detected at 254 nm, to afford (-)-3c (6.40 g, 20.8 mmol, 50%) as a first elution and (+)-3c (6.32 g, 20.6 mmol, 49%) as a second elution. The spectral data were identical to those of the racemic 3c except for optical rotation.CommentCompound (-)-3c: -82.7 (c 0.526, MeOH); t_R = 9.9 min (Chiralpak AD 4.6 mmID × 250mmL, hexane/ethanol = 1/1, 0.5 mL/min, at 254 nm); 99.8% ee. Compound (+)-3c: +83.8 (c 0.474, MeOH); t_R = 19.1 min (Chiralpak AD 4.6 mmID × 250 mmL, hexane/ethanol = 1/1, 0.5 mL/min, at 254 nm); 99.8% ee.

References:

Ruchelman, Alexander L.;Man, Hon-Wah;Chen, Roger;Liu, Wei;Lu, Ling;Cedzik, Dorota;Zhang, Ling;Leisten, Jim;Collette, Alice;Narla, Rama Krishna;Raymon, Heather K.;Muller, George W. [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 21,p. 6356 - 6374] Location in patent:experimental part

5773-80-8 Synthesis