Methyl 2-(8-(nitromethyl)-1,4-dioxaspiro[4.5]decan-8-yl)acetate → 1,4-Dioxa-10-azadispiro[4.2.4^{8}.2^{5}]tetradecan-11-one

HRID 1505691Notes

Reaction equation

HRID 1505691 reaction equation
[N+:1]([CH2:4][C:5]1([CH2:15][C:16]([O:18]C)=O)[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1)([O-])=O>CO.[Pd]>[O:12]1[C:8]2([CH2:13][CH2:14][C:5]3([CH2:15][C:16](=[O:18])[NH:1][CH2:4]3)[CH2:6][CH2:7]2)[O:9][CH2:10][CH2:11]1

Participants

4

Reactant 1

HCID 57795518Methyl 2-(8-(nitromethyl)-1,4-dioxaspiro[4.5]decan-8-yl)acetate

Product 1

HCID 577954141,4-Dioxa-10-azadispiro[4.2.4^{8}.2^{5}]tetradecan-11-oneYield 70.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a slurry of Methyl [8-(nitromethyl)-1,4-dioxaspiro[4.5]dec-8-yl]acetate (1 g, 4.7 mmol) in Methanol (20 mL) was added Pd/C (1 g, 10%) under N2 atmosphere. The reaction mixture was stirred at room temperature under 5 kg/cm2 H2 pressure for 12 h. After completion, the reaction mixture was filtered through celite pad, washed with methanol and the filtrate was concentrated under reduced pressure to afford the title compound as a white solid (0.7 g, 70%). 1H NMR (400 MHz, DMSO-d6) δ 7.46 (s, 1H), 3.83 (s, 4H), 3.00 (s, 2H), 2.00 (s, 2H), 1.56-1.51 (m, 8H).

Workup

  1. filtrationAfter completion, the reaction mixture was filtered through celite pad
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-de3228e0bb804093b6b745d511dbb4ce
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

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