Ethyl 8-(cyanomethyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate → 1,4-Dioxa-10-azadispiro[4.2.4.2]tetradecan-9-one

HRID 2092666Notes

Reaction equation

HRID 2092666 reaction equation
C([O:3][C:4]([C:6]1([CH2:16][C:17]#[N:18])[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1)=O)C.[H][H]>CO.C(O)(=O)C.[Pt](=O)=O>[O:13]1[C:9]2([CH2:14][CH2:15][C:6]3([CH2:16][CH2:17][NH:18][C:4]3=[O:3])[CH2:7][CH2:8]2)[O:10][CH2:11][CH2:12]1

Participants

6

Reactant 2

HCID 58230182Ethyl 8-(cyanomethyl)-1,4-dioxaspiro[4.5]decane-8-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 582301081,4-Dioxa-10-azadispiro[4.2.4.2]tetradecan-9-oneYield 39%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

8-Cyanomethyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (525 mg, obtained in example 121, step 2) was dissolved in methanol (10 mL) and acetic acid (5 mL). Platinum (IV) oxide (235 mg) was added and an atmosphere of hydrogen was introduced at RT. The mixture was stirred under hydrogen at room temperature for 18 hours. The reaction mixture was filtered over dicalite speed plus (Acros Organics) and the solvent was evaporated. The residue was poured into ice/water and was basified with 2M aqueous NaOH solution. The aqueous layer was extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a colorless solid (169 mg, 39%). MS (m/e): 212.2 [MH+].

Workup

  1. filtrationThe reaction mixture was filtered over dicalite speed plus (Acros Organics)
  2. customthe solvent was evaporated
  3. additionThe residue was poured into ice/water
  4. extractionThe aqueous layer was extracted two times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

Sources & evidence

ORD record
ord-8b3d52cccc2c4e6cb1c27fd517470fce
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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