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

HRID 2275529Notes

Reaction equation

HRID 2275529 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 r.m., 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. temperaturecooled
  4. filtration, and then filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-24d95f676cba486c90221686448932a8
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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