Hydrochloric Acid → HCID 57513870, compound

HRID 2262723Notes

Reaction equation

HRID 2262723 reaction equation
[CH2:1]([N:8]1[C:16]2([CH:21]=[CH:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCOCC1>[CH2:1]([N:8]1[C:16]2([CH:17]=[CH:18][NH:19][CH2:20][CH2:21]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15548678HCID 15548678, compound

Product 1

HCID 57513870HCID 57513870, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To solution of tert-butyl 2-benzyl-3-oxo-2,2′,3,3′-tetrahydro-1′H-spiro[isoindole-1,4′-pyridine]-1′-carboxylate (4 mmol) in dioxane (10 ml) is added HCl solution in dioxane (4N, 15 ml, 60 mmol) and the mixture is stirred at rt overnight. The solvent is removed and to the residue is added 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 residue is purified by flash column to give the title compound as an off-white solid.

Workup

  1. customThe solvent is removed and to the residue
  2. additionis added aqueous NaHCO3 solution (30 ml) and EtOAc (30 ml)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (30 ml)
  5. washThe combined extracts are washed with brine (30 ml)
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue is purified by flash column

Sources & evidence

ORD record
ord-ff793d73095c429ca218b3c645af1ffb
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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