HCID 178495702, compound → 5-(Methoxymethyl)oxazolidin-2-one

HRID 1900069Notes

Reaction equation

HRID 1900069 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[O:8][C:7](=[O:9])[N:6](C2C=CC([C@H]3CC[C@H](OCCC#N)CC3)=CC=2)[CH2:5]1>CO.N.[Ni]>[CH3:1][O:2][CH2:3][CH:4]1[O:8][C:7](=[O:9])[NH:6][CH2:5]1

Participants

5

Reactant 1

HCID 178495702HCID 178495702, compound

Product 1

HCID 103131495-(Methoxymethyl)oxazolidin-2-one

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

932 mg (2.6 mmol) of (R)-3-[trans-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-cyclohexyloxy]-propionitrile were dissolved in 60 ml of methanol saturated with dry ammonia gas and hydrogenated in the presence of 0.9 g of Raney-nickel (Type B 113W Degussa). After 3 hours the catalyst was filtered off under suction and the filtrate was evaporated. The residue was dissolved in methylene chloride, washed with water, dried over sodium sulfate, filtered and evaporated. The base was dissolved in alcohol and made acid with ethereal hydrochloric acid. After recrystallization from alcohol-ether there were obtained 825.2 mg of (R)-3-[trans-4-(3-amino-propoxy)-cyclohexyl]-phenyl]-5-methoxymethyl-oxazolidin-2-one.HCl. M.p.: 178°-180°. [α]D =-29.78° (c=1% in CHCl3).

Workup

  1. filtrationAfter 3 hours the catalyst was filtered off under suction
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe base was dissolved in alcohol
  9. customAfter recrystallization from alcohol-ether

Sources & evidence

ORD record
ord-a53690b1a42f419caf4cfc3fb6322405
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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