(RS)-3-[5-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-pyridin-2-yl]-5-methoxymethyl-oxazolidin-2-one → HCID 23371867, compound

HRID 1900052Notes

Reaction equation

HRID 1900052 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:12]=[CH:13][C:14]([N:17]4[CH2:21][CH:20]([CH2:22][O:23][CH3:24])[O:19][C:18]4=[O:25])=[N:15][CH:16]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1>CO.[Pd]>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:12]=[CH:13][C:14]([N:17]4[CH2:21][CH:20]([CH2:22][O:23][CH3:24])[O:19][C:18]4=[O:25])=[N:15][CH:16]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 23371891(RS)-3-[5-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-pyridin-2-yl]-5-methoxymethyl-oxazolidin-2-one

Product 1

HCID 23371867HCID 23371867, compoundYield 38.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.9 g of (RS)-3-[5-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-pyridin-2-yl]-5-methoxymethyl-oxazolidin-2-one and 0.4 g of palladium-on-charcoal (10%) in 150 ml of methanol was hydrogenated at room temperature and normal pressure. After filtering off the catalyst the filtrate was concentrated and the residue was recrystallized from diethyl ether. There was obtained 0.35 g of (RS)-3-[5-(1,4-dioxa-spiro[4,5]decan-8-yl)-pyridin-2-yl]-5-methoxymethyl-oxazolidin-2-one. M.p.: 117°-121°.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationAfter filtering off the catalyst the filtrate
  3. concentrationwas concentrated
  4. customthe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-94cc77ce56954073a515f02d52e28185
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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