HCID 23371882, compound → HCID 23371866, compound

HRID 1900055Notes

Reaction equation

HRID 1900055 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[N:16]=[CH:15][C:14]([N:17]4[CH2:21][CH:20]([CH2:22][O:23][CH3:24])[O:19][C:18]4=[O:25])=[CH:13][CH:12]=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[N:16]=[CH:15][C:14]([N:17]4[CH2:21][CH:20]([CH2:22][O:23][CH3:24])[O:19][C:18]4=[O:25])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 23371882HCID 23371882, compound

Product 1

HCID 23371866HCID 23371866, compoundYield 149.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.8 g of (RS)-3-[6-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-pyridin-3-yl]-5-methoxymethyl-oxazolidin-2-one and 1.1 g of palladium-on-charcoal (10%) in 250 ml of methanol was hydrogenated at room temperature and normal pressure. After filtering off the catalyst the filtrate was concentrated. 1.2 g of (RS)-3-[6-(1,4-dioxa-spiro[4,5]decan-8-yl)-pyridin-3-yl]-5-methoxymethyl-oxazolidin-2-one were obtained. A sample was purified further on silica gel 60 with ethyl acetate as the eluent and boiled with diethyl ether. M.p.: 93°-94°.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationAfter filtering off the catalyst the filtrate
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-b839b2fe695a41c189427688a6ab0d05
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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