Triethylamine → Benzyl 1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

HRID 597840Notes

Reaction equation

HRID 597840 reaction equation
[O:1]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[O:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>C1COCC1.CCOC(C)=O>[O:1]1[C:6]2([CH2:11][CH2:10][N:9]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:8][CH2:7]2)[O:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 27372161,5-Dioxa-9-azaspiro(5.5)undecane

Product 1

HCID 59022466Benzyl 1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylateYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,5-dioxa-9-aza spiro[5.5]undecane (15.0 g, 95.4 mmol) and triethylamine (17.6 mL, 126 mmol) in THF (140 mL) cooled to 0° C. was added dropwise a solution of benzyl chloroformate (14 mL, 97.5 mmol) dissolved in THF (30 mL). The resulting mixture was stirred at room temp for 18 h. After diluting with EtOAc, the mixture was washed with water and brine and dried (Na2SO4). Concentration gave yellow oil that was purified by flash chromatography eluting with 20%-50% EtOAc/hexane to give the title compound as colorless oil (18.9 g, 68% yield). 1H NMR (300 MHz, CDCl3) δ: 7.36-7.27 (5H, m), 5.09 (2H, s), 3.89-3.85 (4H, m), 3.51-3.47 (4H, m), 1.87-1.66 (6H, m). LCMS (M+H) calcd for C16H22NO4: 292.15; found: 292.00.

Workup

  1. washthe mixture was washed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationConcentration
  4. customgave yellow oil that
  5. customwas purified by flash chromatography
  6. washeluting with 20%-50% EtOAc/hexane

Sources & evidence

ORD record
ord-f12ab60e993f4ff590b3bc2e032d02b0
Source dataset
uspto-grants-2011_03
Patent number
US07897593B2

Reaction notes

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