Pyridine → ethyl [4-benzoyl-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl]carbamate

HRID 2247904Notes

Reaction equation

HRID 2247904 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:4][C:3]=1[CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1.N1C=CC=CC=1.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32]>O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:31](=[O:32])[O:33][CH2:34][CH3:35])=[C:3]([CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH:4]=1)(=[O:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 19816012[4-amino-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl] phenylmethanone

Product 1

HCID 53834446ethyl [4-benzoyl-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl]carbamateYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and cooled (10° C.) solution of 13.7 parts of intermediate 57, namely [4-amino-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl] phenylmethanone, in 147 parts of pyridine were added dropwise 7.14 parts of ethyl chloroformate. After stirring for 1 hour at 10° C., the reaction mixture was poured into 700 parts of water. The product was extracted with dichloromethane and the extract was washed with water (3×), dried, filtered and evaporated. The residue was co-evaporated with ethanol (3×) and was then crystallized from ethanol. The product was filtered off, washed with ethanol and 2,2'-oxybispropane and dried in vacuo at 60° C., yielding 14.05 parts (83.5%) of ethyl [4-benzoyl-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl]carbamate; mp. 115.9° C. (interm. 58).

Workup

  1. stirringAfter stirring for 1 hour at 10° C.
  2. extractionThe product was extracted with dichloromethane
  3. washthe extract was washed with water (3×)
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customwas then crystallized from ethanol
  8. filtrationThe product was filtered off
  9. washwashed with ethanol and 2,2'-oxybispropane
  10. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-0d49dedf3cd54aaf9f7bffca061ab53b
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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