Methanol → HCID 178495701, compound

HRID 1900062Notes

Reaction equation

HRID 1900062 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][C:19](=CC#N)[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5]1.[H][H].[CH3:27][OH:28]>[Pd].C>[CH3:27][O:28][C@H:19]1[CH2:18][CH2:17][C@H:16]([C:13]2[CH:14]=[CH:15][C:10]([N:6]3[CH2:5][C@H:4]([CH2:3][O:2][CH3:1])[O:8][C:7]3=[O:9])=[CH:11][CH:12]=2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 887MethanolHCID 54090920HCID 54090920, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178495701HCID 178495701, compound

Reagents, catalysts & solvents 1

HCID 14818447PalladiumcarbonCatalyst

Procedure

1.1 g of (R)-[4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl]-phenyl]-cyclohexylidene]-acetonitrile were dissolved in 50 ml of methanol, treated with 0.2 g of 10% Pd-charcoal and hydrogenated at room temperature at normal pressure until the theoretical hydrogen uptake had taken place. The catalyst was filtered off under suction and the filtrate was evaporated in a vacuum. The oily residue was chromatographed over 15 g of silica gel. Elution was carried out with dichloromethane/ethyl acetate 9:1. The fractions which were pure according to thin-layer chromatography were pooled and crystallized from ethyl acetate/hexane. 0.64 g of (R)-[trans-[4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-cyclohexyl]-acetonitrile was obtained as white crystals of m.p. 90°-91°. ##EQU1##

Workup

  1. filtrationThe catalyst was filtered off under suction
  2. customthe filtrate was evaporated in a vacuum
  3. customThe oily residue was chromatographed over 15 g of silica gel
  4. washElution
  5. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-273f2e55dd4c4f2bbc7728900a9678d6
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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