3-Hydroxypyridine → HCID 91580172, compound

HRID 2100629Notes

Reaction equation

HRID 2100629 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9](=[O:14])[N:8]([CH2:15][CH2:16][OH:17])[C@@H:7]3[CH2:18][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][C@H:6]3[C:5]=2[CH:4]=1)[CH3:2].O[C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9](=[O:14])[N:8]([CH2:15][CH2:16][O:17][C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)[C@@H:7]3[CH2:18][N:19]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:20][C@H:6]3[C:5]=2[CH:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 90726161HCID 90726161, compound

Product 1

HCID 91580172HCID 91580172, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (±)-trans tert-butyl 8-ethyl-4-(2-hydroxyethyl)-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, from Example 86, Part B, (24 mg, 0.064 mmol) in 1 mL of toluene was added 3-hydroxypyridine (9 mg, 0.096 mmol), triphenylphosphine (20 mg, 0.077 mmol) and diethylazodicarboxylate (0.035 mL, 0.077 mmol). The resulting mixture was allowed to stir at ambient temperature for 18 h. The reaction was diluted with ethyl acetate. The organics were washed with sat'd aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo. The residue was purified by flash chromatography (elution with 3:2 to 1:2 hexane/ethyl acetate) to afford 20 mg of the title compound which was contaminated with a small amount of triphenylphosphine oxide. LRMS (ESI): 452.3 (M+H)+.

Workup

  1. washThe organics were washed with sat'd aq NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered through a pad of silica gel
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (elution with 3:2 to 1:2 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c29b956397a740caa6ef97de329c3e15
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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