3-(2-OXO-ETHYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER synthesis

6synthesis methods

Product Name:3-(2-OXO-ETHYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
CAS Number:372159-76-7
Molecular formula:C12H21NO3
Molecular Weight:227.3

948015-72-3 Synthesis

tert-butyl 3-(cyanoMethyl)piperidine-1-carboxylate

948015-72-3
58 suppliers
inquiry

3-(2-OXO-ETHYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

372159-76-7
28 suppliers
inquiry

Yield: 67.8 mg

Reaction Conditions:

with diisobutylaluminium hydride in diethyl ether at -78 - 20; for 4 h;

Steps:

1 tert-butyl 3-(2-oxoethyl)piperidine-1-carboxylate (38)
The cyanide 37 (115.9 mg, 0.52 mmol, 1 eq) is dissolved in 1.8 mL ether and then cooled down to -78 C. DIBAL-H (71 µL, 0.6 mmol, 1.2 eq) is added and the reaction mixture is gradually warmed up to room temperature over 4 h. The reaction was then quenched at -78 C by MeOH and saturated aqueous sodium potassium tartrate solution and stirred for 2 hours at room temperature until the two layers are well separated. The aqueous phase is extracted with Et₂O, the combined organic phase was washed with brine, and dried over Na₂SO₄. Filtration and concentration affords the crude aldehyde 38 (67.8 mg, 58%) which was used without further purification. 1H NMR (300 MHz, Chloroform-d) d 9.80 (t, J = 1.9 Hz, 1H), 3.95 (s, 1H), 3.84 (d, J = 13.4 Hz, 1H), 2.97-2.68 (m, 3H), 2.46-2.19 (m, 2H), 2.05-1.79 (m, 1H), 1.79-1.55 (m, 2H), 1.48 (d, J = 2.0 Hz, 9H), 1.38 (dt, J = 10.8, 3.4 Hz, 1H). HRMS (ESI) : m/z [M+H]⁺ calcd. for C₁₂H₂₂NO₃: 228.15 found: 228.16

References:

ALBERT-LUDWIGS-UNIVERSITÄT FREIBURG WO2021/53158, 2021, A1 Location in patent:Page/Page column 30; 45-46

24424-99-5 Synthesis