HCID 59226578, compound → (4R)-4-(hydroxymethyl)-5-(1-hydroxypropan-2-yl)oxazolidin-2-one

HRID 73591Notes

Reaction equation

HRID 73591 reaction equation
C([O:8][CH2:9][C@@H:10]1[CH:14]([CH:15]([CH3:18])[CH2:16][OH:17])[O:13][C:12](=[O:19])[NH:11]1)C1C=CC=CC=1>CO.[Pd]>[OH:8][CH2:9][C@@H:10]1[CH:14]([CH:15]([CH3:18])[CH2:16][OH:17])[O:13][C:12](=[O:19])[NH:11]1

Participants

4

Reactant 1

HCID 59226578HCID 59226578, compound

Product 1

HCID 59226593(4R)-4-(hydroxymethyl)-5-(1-hydroxypropan-2-yl)oxazolidin-2-oneYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (4R)-4-(benzyloxymethyl)-5-(1-hydroxypropan-2-yl)oxazolidin-2-one (1.0 equiv.) in methanol, at a concentration of 0.1M, was added 10% palladium on carbon (0.1 eq.). The resultant heterogeneous solution was put under an atmosphere of hydrogen and was stirred for 15 hours. At this time the mixture was filtered through a pad of celite eluting with methanol. The volatiles were removed in vacuo yielding (4R)-4-(hydroxymethyl)-5-(1-hydroxypropan-2-yl)oxazolidin-2-one (99%). LCMS (m/z): 176.1 (MH+).

Workup

  1. filtrationAt this time the mixture was filtered through a pad of celite
  2. washeluting with methanol
  3. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-941eb7ae2a454f27b3b672263f261a2b
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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