Phenol → HCID 91563295, compound

HRID 2100628Notes

Reaction equation

HRID 2100628 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].[C:28]1(O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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.Cl>[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:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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 996PhenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 90726161HCID 90726161, compound

Product 1

HCID 91563295HCID 91563295, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent

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 phenol (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 10 mL of 1 N HCl and extracted 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 3:1 hexane/ethyl acetate) to afford 17 mg (59%) of the title compound as an oil. LRMS (ESI): 451.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-6c31439359d34c20bdd7cc3013ec2de2
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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