Formic Acid → Spiro[1,2-benzisothiazole-3,3'-pyrrolidine]1,1-dioxide

HRID 557809Notes

Reaction equation

HRID 557809 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]2([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[S:14](=[O:22])(=[O:21])[NH:13]2)[CH2:9]1)C1C=CC=CC=1.C(O)=O>CO.[Pd]>[NH:8]1[CH2:12][CH2:11][C:10]2([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[S:14](=[O:22])(=[O:21])[NH:13]2)[CH2:9]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 66662102HCID 66662102, compound

Product 1

HCID 66661967Spiro[1,2-benzisothiazole-3,3'-pyrrolidine]1,1-dioxideYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1′-benzylspiro[1,2-benzisothiazole-3,3′-pyrrolidine]1,1-dioxide (170 mg, 0.00054 mol) in methanol were added Pd black (150 mg) and formic acid (0.2 mL, 0.005 mol). The resulting reaction mixture was refluxed overnight, then cooled to room temperature, and then filtered and concentrated to give the desired compound (50 mg, 42% Yield). MS (ESI): 225.1 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d6252a02097e42588a057318ad45aa5f
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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