Sodium Sulfide → HCID 21849647, compound

HRID 617755Notes

Reaction equation

HRID 617755 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:12][C@H:11]([CH2:13]OS(C)(=O)=O)[C@H:10]([CH2:19]OS(C)(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S-2:25].[Na+].[Na+]>CS(C)=O>[C:1]1([CH2:7][N:8]2[CH2:9][CH:10]3[CH2:19][S:25][CH2:13][CH:11]3[CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 86754455HCID 86754455, compound

Product 1

HCID 21849647HCID 21849647, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of cis-1-(phenylmethyl)-3,4-di(methylsulfonyloxy)methylpyrrolidine (9.2 g, mmol), in dry DMSO (48 mL) was added anhydrous sodium sulfide (5.7 g, 73.3 mmol). The dark reaction mixture was heated at 120° C. for 18 h. The cooled reaction mixture was poured into ice H2O (150 mL). The resulting mixture was washed with ether (3×200 mL). The combined organics were dried (MgSO4), filtered and concentrated. The resulting residue was purified by flash chromatography using ethyl acetate as the eluent to afford 4.2 g (19.1 mmol, 78%) of the desired product as a thick yellow oil. HRMS (EI) calcd for C13H17NS 219.1082, found 219.1080. Anal. calcd for C13H17NS: C, 71.19; H, 7.81; N, 6.39. Found: C, 70.82; H, 7.83; N, 6.35.

Workup

  1. customThe dark reaction mixture
  2. customThe cooled reaction mixture
  3. washThe resulting mixture was washed with ether (3×200 mL)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-8d39b185fe90488db132696c0c8d94e2
Source dataset
uspto-grants-1999_09
Patent number
US05952324

Reaction notes

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