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 1694520Notes

Reaction equation

HRID 1694520 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1([CH2:15][N+:16]([O-])=O)[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1>CO.[Ni]>[O:12]1[C:8]2([CH2:13][CH2:14][C:5]3([CH2:4][C:3](=[O:2])[NH:16][CH2:15]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 96%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of (8-nitromethyl-1,4-dioxa-spiro[4.5]dec-8-yl)-acetic acid methyl ester (5.34 g, 19.5 mmol) in 35 mL of methanol was purged with nitrogen. A portion of about 430 mg of Raney 2800 nickel was added. The reaction mixture was purged with hydrogen and a positive pressure of hydrogen was maintained overnight using a balloon. Then, the final mixture was purged with nitrogen and filtered through a pad of celite washing with methanol. The filtrate was concentrated to afford 1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-11-one (3.95 g, 96%) as a white solid.

Workup

  1. customThe reaction mixture was purged with hydrogen
  2. temperaturea positive pressure of hydrogen was maintained overnight
  3. customThen, the final mixture was purged with nitrogen
  4. filtrationfiltered through a pad of celite
  5. washwashing with methanol
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4033ab7ac1d54c689a5d41bb60034305
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

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