HCID 67509425, compound → HCID 67508214, compound

HRID 1770759Notes

Reaction equation

HRID 1770759 reaction equation
C([O:8][CH2:9][CH:10]1[O:14][C:13](=[O:15])[NH:12][C:11]1([CH3:17])[CH3:16])C1C=CC=CC=1>CCO.[Pd]>[OH:8][CH2:9][CH:10]1[O:14][C:13](=[O:15])[NH:12][C:11]1([CH3:17])[CH3:16]

Participants

4

Reactant 1

HCID 67509425HCID 67509425, compound

Product 1

HCID 67508214HCID 67508214, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of 5-((benzyloxy)methyl)-4,4-dimethyloxazolidin-2-one (2.6 g, 11 mmol) in EtOH (40 ml) was added 500 mg of 10% Pd/C (wet, Degussa type E101). The vessel was pressurized with H2 (450 psi) and the suspension stirred for 24 h. An additional 500 mg of 10% Pd/C was added and the reaction was stirred under 450 PSI H2 for 5 days. The mixture was filtered through celite, concentrated in vacuo, and purified by column chromatography (1 to 10% methanol in dichloromethane) to give a clear liquid which solidified to a white solid upon standing (1.8 g, 12 mmol, 100%). 1H NMR (CDCl3, 400 MHz) δ 1.30 (s, 3H), 1.41 (s, 3H), 2.45 (br s, 1H), 3.76-3.81 (m, 1H), 3.87-3.92 (m, 1H), 4.30-4.32 (dd, J=4.4, 7.2 Hz, 1H) 5.59 (br s, H). LRMS (ESI/APCI) m/z 146 [M+H]+.

Workup

  1. stirringthe reaction was stirred under 450 PSI H2 for 5 days
  2. filtrationThe mixture was filtered through celite
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography (1 to 10% methanol in dichloromethane)
  5. customto give a clear liquid which

Sources & evidence

ORD record
ord-f719c8cfcb10420e89c16362b3a8d208
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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