HCID 68950273, compound → (R)-5-(hydroxymethyl)-4-methylmorpholin-3-one

HRID 2384925Notes

Reaction equation

HRID 2384925 reaction equation
C([O:8][CH2:9][C@H:10]1[N:15]([CH3:16])[C:14](=[O:17])[CH2:13][O:12][CH2:11]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][CH2:9][C@H:10]1[N:15]([CH3:16])[C:14](=[O:17])[CH2:13][O:12][CH2:11]1

Participants

5

Reactant 2

HCID 68950273HCID 68950273, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68949899(R)-5-(hydroxymethyl)-4-methylmorpholin-3-oneYield 96.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Prepare a slurry containing 10% Pd/C (137 mg) in MeOH (50 mL). Add a solution of (R)-5-benzyloxymethyl-4-methyl-morpholin-3-one (1.3 g, 5.5 mmol) in MeOH (100 mL). Pressurize with hydrogen gas (50 psi) and stir for 2 h. Filter the reaction through Celite® and elute with MeOH. Concentrate the filtrate to give 767 mg (96%) of the title compound. MS/ES m/z 146.1 [M+H]+.

Workup

  1. customPrepare a slurry
  2. filtrationFilter
  3. customthe reaction through Celite®
  4. washelute with MeOH
  5. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-c9e8ec8211134254813b5e2793dddf21
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

Loading…