ChemicalBook CAS DataBase List 4-(1H-Indol-3-yl)piperidine-1-carboxylic acid tert-butyl ester

4-(1H-Indol-3-yl)piperidine-1-carboxylic acid tert-butyl ester synthesis

7synthesis methods

Product Name:4-(1H-Indol-3-yl)piperidine-1-carboxylic acid tert-butyl ester
CAS Number:155302-28-6
Molecular formula:C18H24N2O2
Molecular Weight:300.4

155302-27-5 Synthesis

TERT-BUTYL 4-(1H-INDOL-3-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE

155302-27-5
38 suppliers
$132.00/1g

4-(1H-Indol-3-yl)piperidine-1-carboxylic acid tert-butyl ester

155302-28-6
38 suppliers
$454.00/250mg

Yield:155302-28-6 95%

Steps:

109.2 Step 2.

Step 2.
Tert-butyl 4-(1H-indol-3-yl)piperidin-1-carboxylate (GEN1-139-2)
Tert-butyl 4-(1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (950 mg, 3.18 mmol) was added to a solution of Pd/C (10%, 200 mg) in tetrahydrofuran (5 mL) and MeOH (5 mL) and the mixture was hydrogenated under H₂ atmosphere at 50°C for 2 hours.
The mixture was cooled to room temperature and filtered through kieselguhr.
The filtrate was concentrated to obtain the desired compound (1.0 g, yield 95%) as a white solid. ¹HNMR (400 MHz, CDCl₃): δ 8.09 (br s, 1H), 7.63 (d, J= 7.6 Hz, 1H), 7.36 (d, J= 8.0 Hz, 1H), 7.21-7.17 (m, 1H), 7.12-7.08 (m, 1H), 6.95 (d, J = 2.0 Hz, 1H), 4.22 (br s, 2H), 3.01 -2.87 (m, 3H), 2.05-2.02 (m, 2H), 1.71-1.62 (m, 2H), 1.49 (s, 9H). MS (ESI): Rt = 1.75 min, m/z 299.4 [M-H]^-; Purity: 91% 254 nm, 70% 214 nm.

References:

EP3960736,2022,A1