Triethylamine → HCID 117986053, compound

HRID 1055622Notes

Reaction equation

HRID 1055622 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C@@:8]23[O:15][C@@:12]([CH:16]([OH:18])[CH3:17])([CH2:13][O:14]2)[C@@H:11]([OH:19])[C@H:10]([OH:20])[C@H:9]3[OH:21])=[CH:4][C:3]=1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=1.C(N(CC)CC)C>CO.[Pd]>[CH2:30]([O:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C:3]2[CH:4]=[C:5]([C@@:8]34[O:15][C@@:12]([CH:16]([OH:18])[CH3:17])([CH2:13][O:14]3)[C@@H:11]([OH:19])[C@H:10]([OH:20])[C@H:9]4[OH:21])[CH:6]=[CH:7][CH:2]=2)=[CH:28][CH:27]=1)[CH3:31]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 117985969HCID 117985969, compound

Product 1

HCID 117986053HCID 117986053, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (1R,2S,3S,4R,5S)-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(1-hydroxyethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol 1 (10.0 g, 21.6 mmol, HPLC: 97.5%) in methanol (80 mL) were added Pd/C (1.5 g, 0.705 mmol, 5%) and triethylamine (5 mL, 32.4 mmol) at room temperature in turn. The mixture was stirred at room temperature under H2 for 20 hours and filtered. The filtrate was concentrated in vacuo. To the residue were added ethyl acetate (80 mL) and water (50 mL) and the resulting mixture was stirred at room temperature for 5 min, then stood for a few minutes and partitioned. The organic layer was washed with saturated aqueous sodium chloride (50 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 30 as a white solid (9.2 g, 99.6%, HPLC: 97.1%). The compound was characterized by the following spectroscopic data: 1H NMR (600 MHz, CD3OD) δ (ppm): 7.43 (s, 1H), 7.38 (d, 1H), 7.26 (t, 1H), 7.15 (d, 1H), 7.11 (d, 2H), 6.82 (d, 2H), 4.18 (d, 1H), 4.01 (m, 3H), 3.95-3.91 (m, 3H), 3.80 (dd, 1H), 3.68 (t, 1H), 3.60 (d, 1H), 1.37 (t, 3H), 1.33 (d, 3H); and MS (ESI, pos. ion) m/z: 417.1[M+H]+.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. additionTo the residue were added ethyl acetate (80 mL) and water (50 mL)
  4. stirringthe resulting mixture was stirred at room temperature for 5 min
  5. waitstood for a few minutes
  6. custompartitioned
  7. washThe organic layer was washed with saturated aqueous sodium chloride (50 mL×2)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7b001df7fa624882ac27c677db4d653a
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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