(R)-2-METHYL-1-((S)-1-PHENYLETHYL)PIPERIDIN-4-ONE synthesis
- Product Name:(R)-2-METHYL-1-((S)-1-PHENYLETHYL)PIPERIDIN-4-ONE
- CAS Number:89467-37-8
- Molecular formula:C14H19NO
- Molecular Weight:217.31
89467-36-7
24 suppliers
$175.00/250 mg
89467-37-8
19 suppliers
inquiry
Yield: 66%
Reaction Conditions:
with (2E)-but-2-enedioic acid in acetone at 5 - 46; for 18 h;
Steps:
4C Preparations 4C. N-(1-(S)-phenylethyl)-2-(R)-methylpiperidin-4-one
N-(1-(S)-PHENYLETHYL)-2 (S)-METHYLPIPERIDIN-4-ONE is epimerized to N- (1- (S)- phenylethyl)-2 (R)-METHYLPIPERIDIN-4-ONE by crystallization directed induced resolution of the diastereomers as follows: Add a solution of 1-(1-S-PHENYLETHYL)-2 (S)-1NETHYLPIPERIDIN-4-ONE (900 g, 4.14 mole) in acetone (1 L) to a suspension OF FUMARIC acid (432 g, 3.72 mole) in acetone (6.2 L) at 22°C. Heat the reaction mixture at 46°C to gradually TRA7ESFORRN the mixture to a suspension. Distill off part of the solvent (3.6 L) and stir until the diastereoisomeric ratio (S, 2R)/ (S, 2S) is 66/34 by PMR. The suspension is then stirred for 16 HR. at 20°C during which time the ratio (S, 2R)/ (S, 2S) increases further to 74/26. Cool the mixture to 5°C and stir for 2 hr. Filter off the solid, wash with cold acetone (L L, 5°C), and dry under vacuum to obtain the title compound (910 g, 66% yield, 91/9 diastereoisomeric ratio, 44/56 diastereoisomeric ratio in the mother liquors).
References:
ELI LILLY AND COMPANY WO2004/94380, 2004, A1 Location in patent:Page 28; 30
35172-85-1
1 suppliers
inquiry
2627-86-3
544 suppliers
$10.60/1gm:
89467-37-8
19 suppliers
inquiry
89467-36-7
24 suppliers
$175.00/250 mg
2627-86-3
544 suppliers
$10.60/1gm:
![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
1000210-73-0
0 suppliers
inquiry
89467-37-8
19 suppliers
inquiry
89467-36-7
24 suppliers
$175.00/250 mg