N-Benzyl-1,4-dioxaspiro[4.5]decan-8-amine → 1,4-Dioxaspiro[4.5]decan-8-amine

HRID 1455375Notes

Reaction equation

HRID 1455375 reaction equation
C1(C[NH:8][CH:9]2[CH2:18][CH2:17][C:12]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:11][CH2:10]2)C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[O:13]1[C:12]2([CH2:17][CH2:18][CH:9]([NH2:8])[CH2:10][CH2:11]2)[O:16][CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 11791515N-Benzyl-1,4-dioxaspiro[4.5]decan-8-amine

Product 1

HCID 146343151,4-Dioxaspiro[4.5]decan-8-amineYield 127.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

20% Palladium hydroxide (1.00 g) was carefully wetted down under nitrogen with methanol (50 mL) then N-(phenylmethyl)-1,4-Dioxaspiro[4.5]decan-8-amine (7.91 g) in methanol (50 mL) was added. The mixture was hydrogenated on a Parr shaker for 20 hours. Worked up by filtering off the catalyst under nitrogen through fiberglass filter paper. The filtrate was stripped to give 1,4-dioxaspiro[4.5]decan-8-amine (6.40 g) as an oily solid. Yield=100%. LCMS detects (M+H)+=158.1.

Workup

  1. filtrationby filtering off the catalyst under nitrogen through fiberglass
  2. filtrationfilter paper

Sources & evidence

ORD record
ord-df1e976848694f44961d2db233594564
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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