HCID 67282369, compound → HCID 25018649, compound

HRID 913030Notes

Reaction equation

HRID 913030 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[C:13]([CH:16]([OH:21])[C:17]([F:20])([F:19])[F:18])=[CH:12][NH:11][C:10]=1[CH3:22])C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[C:14](=[O:15])[C:13]([CH:16]([OH:21])[C:17]([F:20])([F:18])[F:19])=[CH:12][NH:11][C:10]=1[CH3:22]

Participants

4

Reactant 1

HCID 67282369HCID 67282369, compound

Product 1

HCID 25018649HCID 25018649, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 3-benzyloxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (1.00 g, 3.19 mmol) and methanol (30 mL) was sonicated to give a clear solution. Pd/C (10 wt %, dry basis, on activated carbon, wet, Degussa type E101 NE/W, 0.158 g) was added. The debenzylation reaction was conducted under a hydrogen atmosphere pressurized to 50 psi. The reaction was completed in 20 min. The reaction mixture was diluted with methanol (30 mL), sonicated for 10 min. A CELITE™ bed was prepared on a sintered glass, and washed with 6M HCl (100 mL), followed by water (7×50 mL) and then methanol (2×50 mL) under suction. The reaction mixture was filtered through the pre-treated CELITE™ bed. The filtrate was collected and concentrated in vacuo to give 3-hydroxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one as a solid product (0.59 g, 83% yield, HPLC Method 1 (Example 24), RT=7.9 min, HPLC purity (peak percent area): 99.5% at λ=280 nm). 1H NMR (DMSO-d6) δ ppm: 11.72, (br s, 1H), 7.51 (s, 1H), 5.32 (q, J=7.4 Hz, 1H), 2.20 (s, 3H). MS-ESI (m/z) 224.2 [M+1]+, 206.2 (100%), 186.2, 178.2, 158.2.

Workup

  1. customwas sonicated
  2. customto give a clear solution
  3. customThe debenzylation reaction
  4. customsonicated for 10 min
  5. customA CELITE™ bed was prepared on a sintered glass
  6. washwashed with 6M HCl (100 mL)
  7. filtrationThe reaction mixture was filtered through the pre-treated CELITE™ bed
  8. customThe filtrate was collected
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae38b6528b364956b03530001ad23968
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

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