Pyridine → HCID 90426757, compound

HRID 718160Notes

Reaction equation

HRID 718160 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][CH:5]([C:8](=[NH:12])[O:9][CH2:10][CH3:11])[CH2:4][CH2:3]1.N1C=CC=CC=1.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(Cl)Cl.CCCCCC.CCOC(C)=O>[CH2:23]([O:22][C:20]([N:12]=[C:8]([CH:5]1[CH2:6][CH2:7][O:2][CH2:3][CH2:4]1)[O:9][CH2:10][CH3:11])=[O:21])[CH3:24]

Participants

6

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 86726984HCID 86726984, compound

Product 1

HCID 90426757HCID 90426757, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl tetrahydro-2H-pyran-4-carbimidate hydrochloride (1.646 g, 8.50 mmol) was suspended in DCM (21.25 mL) and cooled to 0° C. Pyridine (3.09 mL, 38.2 mmol) was added and the solution was stirred for 15 min. Ethyl chloroformate (1.384 g, 12.75 mmol) was added dropwise. The reaction mixture was allowed to warm to RT and stir overnight. The reaction mixture was diluted with 50% hexane/EtOAc and the resulting suspension was filtered through a plug of diatomaceous earth. The filtrate was concentrated under reduced pressure and the residue dried under high vacuum for several hours to yield ethyl N-ethoxycarbonyltetrahydro-2H-pyran-4-carbimidate (1.80 g, 92%). 1H NMR (400 MHz, DMSO-d6): δ 4.12 (m, 2H), 4.07 (m, 2H), 3.85-3.83 (m, 2H), 3.31-3.24 (m, 2H), 2.69-2.68 (m, 1H), 1.69-1.68 (m, 4H), 1.23 (m, 6H).

Workup

  1. temperatureto warm to RT
  2. stirringstir overnight
  3. filtrationthe resulting suspension was filtered through a plug of diatomaceous earth
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue dried under high vacuum for several hours

Sources & evidence

ORD record
ord-5d4e0c4c08f54412bbd3ad5f36ec099d
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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