ChemicalBook CAS DataBase List (2R)-1-methyl-2-Piperidinecarboxylic acid

(2R)-1-methyl-2-Piperidinecarboxylic acid synthesis

5synthesis methods

Product Name:(2R)-1-methyl-2-Piperidinecarboxylic acid
CAS Number:41447-17-0
Molecular formula:C7H13NO2
Molecular Weight:143.18

50-00-0 Synthesis

50-00-0
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1723-00-8
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(2R)-1-methyl-2-Piperidinecarboxylic acid

41447-17-0
71 suppliers
$20.00/100mg

Yield:41447-17-0 100%

Reaction Conditions:

with 5%-palladium/activated carbon;hydrogen in methanol;water; for 20 h;

Steps:

24 4.1.24
(R)-1-Methylpiperidine-2-carboxylic acid (13)

37% Aqueous solution of formaldehyde (1.26 mL, 16.9 mmol) was added to a mixture of (2R)-piperidine-2-carboxylic acid (2.00 g, 15.5 mmol) and 5% Pd/C (500 mg) in MeOH (20 mL).
After the reaction mixture was purged with H₂ gas, additional formaldehyde (0.60 mL, 8.06 mmol) was added, and stirred under H₂ atmosphere for 20 h.
The reaction mixture was filtered through a pad of Celite, and washed with MeOH (200 mL).
The filtrate was concentrated by rotary evaporation to afford analytically pure amino acid 8 (2.23 g, quantitative yield) as a white solid, which was used in the next step without further purification. TLC: R_f 0.25 (1:1 CH₂Cl₂/MeOH). Mp: 208-210 °C. [α]_D^27.1 = + 67.6 (c 1.27, MeOH). IR (KBr, film): 3407, 2950, 1615, 1399 cm^-1. 1H NMR (400 MHz, CDCl3): d8.22 (br s, 1H), 3.64 (d, 1H, J = 12.0 Hz), 3.28 (m, 1H), 2.86 (s,3H), 2.70 (m, 1H), 2.34 (d, 1H, J = 14.4 Hz), 2.00-1.74 (m, 4H),1.46 (m, 1H). 13C NMR (100 MHz, DMSO-d6): d 170.4, 68.3, 53.3,42.3, 28.0, 23.1, 21.8. HRMS (ESI) m/z calculated for C7H13NO2143.0946, found 143.0947.