HCID 67281550, compound → HCID 67281725, compound

HRID 913034Notes

Reaction equation

HRID 913034 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][N:11]([CH3:22])[C:10]=1[CH3:23])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][N:11]([CH3:22])[C:10]=1[CH3:23]

Participants

4

Reactant 1

HCID 67281550HCID 67281550, compound

Product 1

HCID 67281725HCID 67281725, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

3-Benzyloxy-1,2-dimethyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (0.97 g, 2.96 mmol) in methanol (30 mL) was debenzylated with Pd/C (10 wt. %, dry basis, on activated carbon, wet, Degussa type E101 NE/W, 0.15 g) as catalyst under a hydrogen atmosphere at 50 psi pressure. The reaction was completed in 10 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-1,2-dimethyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one as a solid product (0.43 g, 61% yield, HPLC Method 1 (Example 24), RT=9.4 min, HPLC purity (peak percent area): 99.8% at λ=280 nm). 1H NMR (DMSO-d6) δ ppm: 7.72 (s, 1H), 5.34 (q, J=7.3 Hz, 1H), 3.71 (s, 3H), 2.27 (s, 3H); MS (m/z) 238.1 [M+1]+, 220.2 (100%), 192.3, 172.1.

Workup

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

Sources & evidence

ORD record
ord-1f1c51536c2944ffb58cfc080972a3a5
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

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