8-(Nitromethyl)-1,4-dioxaspiro[4.5]decan-8-ol → 8-(Aminomethyl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1363545

Reaction equation

HRID 1363545 reaction equation
[N+:1]([CH2:4][C:5]1([OH:15])[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1)([O-])=O>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:1][CH2:4][C:5]1([OH:15])[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1

Participants

4

Reactant 1

HCID 468356938-(Nitromethyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 434366478-(Aminomethyl)-1,4-dioxaspiro[4.5]decan-8-olYield 530.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 8-(nitromethyl)-1,4-dioxaspiro[4.5]decan-8-ol (16.0 g, 13.8 mmol) and 20% palladium hydroxide on carbon (3.2 g) in ethanol (160 mL) was hydrogenated at 50 psi (3.5×105 Pa) for 5 d on a Parr apparatus. The reaction mixture was filtered through CELITE filter agent and the filtrate was concentrated to give 8-(aminomethyl)-1,4-dioxaspiro[4.5]decan-8-ol as a clear oil (13.7 g, 99%) that solidified upon standing overnight.

Workup

  1. filtrationThe reaction mixture was filtered through CELITE
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c49b7fac5cc446fe9b1f2a7672548365
Source dataset
uspto-grants-2011_02
Patent number
US07884207B2

Linked notes

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