HCID 68612253, compound → HCID 68613132, compound

HRID 2095312Notes

Reaction equation

HRID 2095312 reaction equation
C([O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C@H:15]2[CH2:17][C@@H:16]2[CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:14]=1)C1C=CC=CC=1>CCOC(C)=O.CO.[Pd]>[CH2:20]([O:19][CH2:18][C@H:16]1[CH2:17][C@@H:15]1[C:13]1[CH:14]=[C:9]([OH:8])[CH:10]=[N:11][CH:12]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 1

HCID 68612253HCID 68612253, compound

Product 1

HCID 68613132HCID 68613132, compoundYield 84.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(benzyloxy)-5-[(1S,2S)-2-(benzyloxymethyl)cyclopropyl]pyridine (210 mg, 608 μmol) in EtOAc (10 mL) and methanol (5.0 mL) was added 10% palladium on carbon (42 mg). The atmosphere was exchanged with H2 (3 times), and the mixture was stirred under H2 for 4 h. The resulting mixture was filtered through a cotton plug, and the filtrate was concentrated and azeotroped with toluene (3×5 mL) to give 5-[(1S,2S)-2-(benzyloxymethyl)cyclopropyl]-3-pyridinol as a light-yellow oil (131 mg, 84%).

Workup

  1. filtrationThe resulting mixture was filtered through a cotton plug
  2. concentrationthe filtrate was concentrated
  3. customazeotroped with toluene (3×5 mL)

Sources & evidence

ORD record
ord-df94645e25df4307bb4d8601fd77fc3b
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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