Sodium Hydroxide → HCID 67154626, compound

HRID 83086Notes

Reaction equation

HRID 83086 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([CH2:16][C:15]3[C:10](=[N:11][CH:12]=[C:13](/[CH:17]=[CH:18]/[C:19]([O:21]CC)=[O:20])[CH:14]=3)[NH:9][C:8]2=[O:24])[CH2:4][CH2:3]1.[OH-].[Na+].C(Cl)[Cl:28].CO>C(Cl)Cl.CCO>[ClH:28].[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:16][C:15]3[C:10](=[N:11][CH:12]=[C:13](/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])[CH:14]=3)[NH:9][C:8]2=[O:24])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226129Dichloromethane methanolHCID 68338070HCID 68338070, compound

Product 1

HCID 67154626HCID 67154626, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-ethyl 3-(1′-methyl-2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-6-yl)acrylate (95 mg, 0.288 mmol) in DCM (2 mL) and EtOH (2 mL) was added 1N aqueous sodium hydroxide (1 mL, 1.000 mmol) and the reaction was stirred at rt overnight, after which TLC (DCM/MeOH, 9:1) showed full conversion. Next, the mixture was concentrated and the residue acidified with 1N HCl (5 mL) and stirred for 1 h. The resulting white solids were isolated by filtration, washed with H2O and Et2O and dried on the filter. The product (47 mg, 48%) was obtained as an off-white solid.

Workup

  1. concentrationNext, the mixture was concentrated
  2. stirringstirred for 1 h
  3. customThe resulting white solids were isolated by filtration
  4. washwashed with H2O and Et2O
  5. customdried on the filter

Sources & evidence

ORD record
ord-0eb5533118bf45e9bca79a5c6d570320
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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