Stannous chloride dihydrate → HCID 66932414, compound

HRID 2046754Notes

Reaction equation

HRID 2046754 reaction equation
[CH3:1][O:2][C:3](=[O:33])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:29](=[CH:30][CH:31]=1)[O:28][C:11]1([CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=3)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:32].O.O.Cl[Sn]Cl.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].C(=O)(O)[O-].[Na+]>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:33])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:29](=[CH:30][CH:31]=1)[O:28][C:11]1([CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=3)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:32]

Participants

6

Reactant 4

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 9855836Potassium sodium tartarateHCID 66932419HCID 66932419, compound

Product 1

HCID 66932414HCID 66932414, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(E)-3-{1′-[2-(4-Nitro-phenyl-)ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (377 mg, 0.833 mmol) was dissolved in AcOEt. SnCl2.2H2O (753 mg, 3.35 mmol) was added and the mixture heated under reflux for 12 h. After cooling down to room temperature the solution was treated with an aqueous solution of sodium potassium tartrate and sodium bicarbonate, and the organic phase was separated, dried and evaporated. The crude product was purified by column chromatography (eluent:DCM/MeOH 99:1 to 97:3) to give (E)-3-{1′-[2-(4-amino-phenyl)-ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (225 mg) as a light brown solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 12 h
  3. customthe organic phase was separated
  4. customdried
  5. customevaporated
  6. customThe crude product was purified by column chromatography (eluent:DCM/MeOH 99:1 to 97:3)

Sources & evidence

ORD record
ord-d499aef1e7544e88b3cb677fe32d2a11
Source dataset
uspto-grants-2013_11
Patent number
US08592444B2

Reaction notes

Loading…