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 2099691Notes

Reaction equation

HRID 2099691 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-0c70af1208af4275ab479680b3b7e7df
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

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