Benzyl 1,4-dioxa-7-azaspiro[4.4]nonane-7-carboxylate → 1,4-Dioxa-7-azaspiro[4.4]nonane

HRID 1409012Notes

Reaction equation

HRID 1409012 reaction equation
[O:1]1[C:5]2([CH2:9][CH2:8][N:7](C(OCC3C=CC=CC=3)=O)[CH2:6]2)[O:4][CH2:3][CH2:2]1>CO.[OH-].[Pd+2].[OH-]>[O:1]1[C:5]2([CH2:9][CH2:8][NH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 15165037Benzyl 1,4-dioxa-7-azaspiro[4.4]nonane-7-carboxylate

Product 1

HCID 151650391,4-Dioxa-7-azaspiro[4.4]nonaneYield 100.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 1,4-dioxa-7-azaspiro[4.4]nonane-7-carboxylate (1.1 g) in methanol (30 mL) was added palladium(II) hydroxide (100 mg) at room temperature. The mixture was stirred for 2.5 hr under a hydrogen atmosphere (0.4 MPa). Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (540 mg) as a dark orange liquid.

Workup

  1. customInsoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-35e021b7ffbd4c1a8f3e29aa8486db50
Source dataset
uspto-grants-2014_12
Patent number
US08921354B2

Reaction notes

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