3A-BENZYL-2-METHYL-2,3A,4,5,6,7-HEXAHYDRO-3H-PYRAZOLO[4,3-C]PYRIDIN-3-ONE L-TARTARATE synthesis
- Product Name:3A-BENZYL-2-METHYL-2,3A,4,5,6,7-HEXAHYDRO-3H-PYRAZOLO[4,3-C]PYRIDIN-3-ONE L-TARTARATE
- CAS Number:193274-37-2
- Molecular formula:
- Molecular Weight:0
![3A-BENZYL-2-METHYL-4,5,6,7-TETRAHYDRO-2H-PYRAZOLO[4,3-C]PYRIDIN-3(3AH)-ONE](/CAS/20180601/GIF/193274-04-3.gif)
Yield:193274-37-2 87%
Reaction Conditions:
in water;acetone at 50; for 70 h;Inert atmosphere;
Steps:
4.1.1. Synthesis of 3aR-benzyl-2-methyl-4,5,6,7-tetrahydro-2Hpyrazolo[4,3-c]pyridin-3(3aH)-one.L-tartrate [(R)-2.L-tartaric acid
(3.092 g, 20.6 mmol) in acetone (80 mL) and H2O (3.2 mL) washeated at 50 C under N2 for 70 h, during which time the reactionmixture became a thick suspension. The reaction mixture wasslowly cooled to 23 C and filtered to give a solid that was washedwith acetone (3 50 mL) and dried in vacuo to give 7.034 g (87%yield) of (R)-2.L-tartaric acid as a white solid. An aliquot of theL-tartaric acid salt was treated with triethylamine in CH2Cl2 atroom temperature to provide (R)-2 which was subjected to chiralHPLC analysis for ee determination (98% ee; Figs. S1 and S2). 1HNMR (CD3OD) d 7.20-7.19 (m, 3H), 7.08-7.07 (d, J = 6.2 Hz, 2H),4.48 (s, 2H), 3.63-3.60 (m, 1H), 3.54-3.43 (m, 2H), 3.30-3.28 (m,2H), 3.07 (d, J = 13.5 Hz, 1H), 2.92-2.87 (m, 2H), 2.86-2.78 (m,1H), 2.63 (d, 13.1 Hz, 1H); MS m/e 244 (M++1). Elemental anal.calcd for C18H23N3O71.5H2O: C, 51.42; H, 6.23; N, 10.00. Found:C, 51.19; H, 6.04; N, 9.97.
References:
Rose, Colin R.;Zawistoski, Michael P.;Lefker, Bruce A.;Mangano, F. Michael;Wright, Ann S.;Carpino, Philip A. [Bioorganic and Medicinal Chemistry,2017,vol. 25,# 3,p. 1000 - 1003]
![TERT-BUTYL 3A-BENZYL-2-METHYL-3-OXO-3A,4,6,7-TETRAHYDRO-2H-PYRAZOLO[4,3-C]PYRIDINE-5(3H)-CARBOXYLATE](/CAS/20180527/GIF/193274-02-1.gif)