Dichloromethane → 1,4-Dioxaspiro[4.5]decan-8-amine

HRID 1483826Notes

Reaction equation

HRID 1483826 reaction equation
C([NH:8][CH:9]1[CH2:18][CH2:17][C:12]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:11][CH2:10]1)C1C=CC=CC=1.C(Cl)Cl>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

5

Reactant 2

HCID 6344DichloromethaneHCID 11791515N-Benzyl-1,4-dioxaspiro[4.5]decan-8-amine

Product 1

HCID 146343151,4-Dioxaspiro[4.5]decan-8-amineYield 110%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of N-benzyl-1,4-dioxaspiro[4.5]decan-8-amine (3 g, 12.2 mmol) and Palladium hydroxide (0.9 g) in MeOH (120 mL) was hydrogenated under 50 psi of H2 at room temperature. The mixture was stirred at room temperature for 24 h. TLC (CH2Cl2:MeOH=10:1) showed the reaction was complete. The mixture was filtered and the filtrated was concentrated in vacuo to give 1,4-dioxaspiro[4.5]decan-8-amine (2.1 g, 110%) as a brown oil.

Workup

  1. customwas hydrogenated under 50 psi of H2 at room temperature
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrated was concentrated in vacuo

Sources & evidence

ORD record
ord-36034387498245eebfea7a5ec263a44e
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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