Ethanol → 1,4-Dioxa-10-azadispiro[4.2.4.2]tetradecan-9-one

HRID 1477951Notes

Reaction equation

HRID 1477951 reaction equation
[N+:1]([CH2:4][C:5]1([CH2:15][C:16](OCC)=O)[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1)([O-])=O.CC[OH:23]>[Ni]>[O:12]1[C:8]2([CH2:13][CH2:14][C:5]3([CH2:15][CH2:16][NH:1][C:4]3=[O:23])[CH2:6][CH2:7]2)[O:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 702EthanolHCID 59505535Ethyl 2-(8-(nitromethyl)-1,4-dioxaspiro[4.5]decan-8-yl)acetate

Product 1

HCID 582301081,4-Dioxa-10-azadispiro[4.2.4.2]tetradecan-9-oneYield 83.8%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a solution of ethyl 2-(8-(nitromethyl)-1,4-dioxaspiro[4.5]decan-8-yl)acetate (109 g, 379.38 mmol) in EtOH (600 mL) was added Raney Ni (10 g). The reaction mixture was stirred under H2 atmosphere at rt for 72 h and filtered. The filter cake was washed with a mixture of DCM and MeOH (1/1 (v/v), 500 mL). The filtrate was concentrated in vacuo and the residue was washed with a mixture of PE and EtOAc (10/1 (v/v), 800 mL) and filtered to give the product as a white solid (67 g, 83.8%).

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with a mixture of DCM and MeOH (1/1 (v/v), 500 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. washthe residue was washed with a mixture of PE and EtOAc (10/1 (v/v), 800 mL)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-4a71a13f0983438ca8ca51928fe7b655
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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