Trifluoroacetic acid → 6-Benzyl-8-nitro-2-oxa-6-aza-spiro[3.4]octane

HRID 539981Notes

Reaction equation

HRID 539981 reaction equation
[CH2:1]([N:8]([CH2:14]OC)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:17]([CH:20]=[C:21]1[CH2:24][O:23][CH2:22]1)([O-:19])=[O:18].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]1[CH2:9][CH:20]([N+:17]([O-:19])=[O:18])[C:21]2([CH2:24][O:23][CH2:22]2)[CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 533465963-(Nitromethylidene)oxetane

Product 1

HCID 712547596-Benzyl-8-nitro-2-oxa-6-aza-spiro[3.4]octaneYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl-methoxymethyl-trimethylsilanylmethyl-amine (3.0 g, 12.6 mmol) and 3-nitromethylene-oxetane (1.38 g, 12.0 mmol) in dichloromethane (60 mL) was added trifluoroacetic acid (0.93 mL, 12.6 mmol) dropwise. The mixture was stirred at room temperature for 2 hours, quenched with sodium carbonate, extracted with dichloromethane. The organic layer was dried over sodium sulfate, concentrated in vacuo. The residue was purified by column chromatography on silica gel to give 2 g of product as colorless oil. It was used for next step without further purification.

Workup

  1. customquenched with sodium carbonate
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1685039ec598424198255aa497d5deb0
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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