Triethylamine → (R)-1-Ethylcarbamoylpiperidine-2-carboxylic acid

HRID 1828637Notes

Reaction equation

HRID 1828637 reaction equation
[CH2:1]1[CH2:6][C@@H:5]([C:7]([OH:9])=[O:8])[NH:4][CH2:3][CH2:2]1.[CH2:10]([N:12]([CH2:15]C)CC)[CH3:11].ClC(OCC)=[O:19]>ClCCl>[CH2:10]([NH:12][C:15]([N:4]1[CH2:3][CH2:2][CH2:1][CH2:6][C@@H:5]1[C:7]([OH:9])=[O:8])=[O:19])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 439227Pipecolic acid, (-)-

Product 1

HCID 54508361(R)-1-Ethylcarbamoylpiperidine-2-carboxylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

L-Pipecolinic acid (0.50 g, 0.004 mole) in dry dichloromethane (10 ml) was cooled to 0° C. under argon and treated with triethylamine (0.65 ml. 0.0046 mole) followed dropwise by ethyl chloroformate (0.37 ml, 0.004 mole) in dry dichloromethane (2 ml). The mixture was stirred overnight at room temperature after which it was diluted with dichioromethane, washed with 5M hydrochloric acid and the organic layer dried (magnesium sulfate) and evaporated in vacuo to afford the title compound 0.60 g (77%) as an orange oil; 1H NMR (CDCl3) 1.12-1.84 (8H, m), 2.15-2.40 (1H, m), 2.88-3.20 (1H, m), 3.90-4.28 (3H, m), 4.77-5.07 (1H, m), 5.68-6.82 (1H, br s),

Workup

  1. washwashed with 5M hydrochloric acid
  2. dry with materialthe organic layer dried (magnesium sulfate)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-caad8e487343420891793bc349965af9
Source dataset
uspto-grants-2006_06
Patent number
USRE039128E1

Reaction notes

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