HCID 57513870, compound → HCID 57513871, compound

HRID 2262724Notes

Reaction equation

HRID 2262724 reaction equation
[CH2:1]([N:8]1[C:16]2([CH:21]=[CH:20][NH:19][CH2:18][CH2:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O.[Pd]>[CH2:1]([N:8]1[C:16]2([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 57513870HCID 57513870, compound

Product 1

HCID 57513871HCID 57513871, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-benzyl-2′,3′-dihydro-1′H-spiro[isoindole-1,4′-pyridin]-3(2H)-one (3.6 mmol) in HOAc (20 ml) is added 10% Pd on C (100 mg) and the mixture is hydrogenated at 50 psi overnight. The catalyst is filtered and washed with methanol (2×10 ml) and the combined filtrate is evaporated to dryness. The residue is partitioned between aqueous NaHCO3 solution (30 ml) and EtOAc (30 ml). The layers are separated and the aqueous layer is extracted with EtOAc (30 ml). The combined extracts are washed with brine (30 ml), dried over Na2SO4 and evaporated. The resulting title product as a light yellow solid is used in the next step without further purification.

Workup

  1. customis hydrogenated at 50 psi overnight
  2. filtrationThe catalyst is filtered
  3. washwashed with methanol (2×10 ml)
  4. customthe combined filtrate is evaporated to dryness
  5. customThe residue is partitioned between aqueous NaHCO3 solution (30 ml) and EtOAc (30 ml)
  6. customThe layers are separated
  7. extractionthe aqueous layer is extracted with EtOAc (30 ml)
  8. washThe combined extracts are washed with brine (30 ml)
  9. dry with materialdried over Na2SO4
  10. customevaporated
  11. customThe resulting title product as a light yellow solid is used in the next step without further purification

Sources & evidence

ORD record
ord-6cd2df8e2b4c47888c612dbc2d8f8911
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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