Triethylamine → HCID 53841393, compound

HRID 1923413Notes

Reaction equation

HRID 1923413 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[C@@H:5]1[CH2:10][CH2:9][CH2:8][NH:7][CH2:6]1)[CH3:2].[CH2:12]([N:14]([CH2:17]C)CC)[CH3:13].ClC(OCC)=[O:21]>ClCCl>[CH2:12]([NH:14][C:17]([N:7]1[CH2:8][CH2:9][CH2:10][C@@H:5]([C:4]([O:3][CH2:1][CH3:2])=[O:11])[CH2:6]1)=[O:21])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 185582ethyl (3R)-piperidine-3-carboxylate

Product 1

HCID 53841393HCID 53841393, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(R)-Ethylnipecotate (J. Org. Chem., 56, 1991, 1166-1170) (3.0 g, 0.019 mole) in dry dichloromethane (50 ml) was cooled to 0° C. under argon. Triethylamine (3.19 ml, 0.023 mole) was added, followed dropwise by ethyl chloroformate (1.83 ml, 0.019 mole) in dry dichloromethane (6 ml) and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with dichloromethane, washed with water, dried (magnesium sulfate) and evaporated in vacuo to afford the title compound 3.45 g (79%) as a colourless oil; 1H NMR (CDCl3) 1.28 (6H, t, J 7 Hz), 1.38-1.82 (3H, m), 2.00-2.15 (1H, m), 2.38-2.55 (1H, m), 2.77-3.13 (2H, m), 3.91-4.04 (1H, m), 4.07-4.35 (5H, m).

Workup

  1. washwashed with water
  2. dry with materialdried (magnesium sulfate)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-062b5eaef7924cd187b004fd5c05dfd5
Source dataset
uspto-grants-2012_05
Patent number
USRE043390E1

Reaction notes

Loading…