1,4-Dioxa-8-azaspiro(4.5)decane → 8-[(2,6-Dimethoxyphenyl)methyl]-1,4-dioxa-8-azaspiro[4.5]decane

HRID 659092Notes

Reaction equation

HRID 659092 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[C:14]=1[CH:15]=O.[H][H]>CO.[Pd]>[CH3:22][O:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:13]([O:12][CH3:11])[C:14]=1[CH2:15][N:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 964042,6-DimethoxybenzaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 689499198-[(2,6-Dimethoxyphenyl)methyl]-1,4-dioxa-8-azaspiro[4.5]decaneYield 105.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1,4-dioxa-8-azaspiro[4,5]decane (19 mL, 0.146 mol), 2,6-dimethoxybenzaldehyde (26.7 g) and 10% Pd/C (wet, 4 g) in methanol (150 mL) was treated with hydrogen (50 psi) for 16 h. The reaction mixture was then filtered and concentrated to give 45 g of the title intermediate as a yellow solid.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-07cf94c060854daf8ea8b643db1d645e
Source dataset
uspto-grants-2011_12
Patent number
US08080565B2

Reaction notes

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