Stannous chloride dihydrate → HCID 93058138, compound

HRID 2284846Notes

Reaction equation

HRID 2284846 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[C:18]([O:20][CH3:21])=[O:19])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.O.O.Cl[Sn]Cl>CCOC(C)=O.[OH-].[Na+]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[C:18]([O:20][CH3:21])=[O:19])(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 819487HCID 819487, compound

Product 1

HCID 93058138HCID 93058138, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (S)-methyl 1-((4-nitrophenyl)sulfonyl)pyrrolidine-2-carboxylate (642 mg, 2.0 mmol) in EtOAc (10 mL) was added SnCl2.2H2O (2.02 g, 9.0 mmol). The resulting mixture was stirred at room temperature for 2 d and diluted with EtOAc (50 mL) and 1 N NaOH (10 mL). The layers were separated and the aqueous phase re-extracted with EtOAc (2×50 mL). The combined organic phases were washed with brine (30 mL) and dried over MgSO4. The mixture was filtered and the solvent was removed in vacuo to yield the title compound as a white solid (531 mg, 93%).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase re-extracted with EtOAc (2×50 mL)
  3. washThe combined organic phases were washed with brine (30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationThe mixture was filtered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-14ce9dcee7a04908954a267221a5978d
Source dataset
uspto-grants-2015_09
Patent number
US09145409B2

Reaction notes

Loading…