1,5-Dioxa-8-azaspiro[5.4]decane benzyl carbamate → 6,10-Dioxa-2-azaspiro[4.5]decane

HRID 846691Notes

Reaction equation

HRID 846691 reaction equation
C(NC(=O)O)C1C=CC=CC=1.[O:12]1[C:17]2([CH2:21][CH2:20][NH:19][CH2:18]2)[O:16][CH2:15][CH2:14][CH2:13]1.[H][H]>CO.[Pd]>[O:12]1[C:17]2([CH2:21][CH2:20][NH:19][CH2:18]2)[O:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 867460631,5-Dioxa-8-azaspiro[5.4]decane benzyl carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 198833386,10-Dioxa-2-azaspiro[4.5]decane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The protecting group was removed by dissolving 2.09 g (7.5 mmol) of 1,5-dioxa-8-azaspiro[5.4]decane benzyl carbamate, from Step 1, in 100 mL of methanol, adding 0.50 g of 20% Pd/C, and hydrogenating at room temperature under 4 atm of hydrogen for 24 hours. The catalyst was removed by filtration, then the solvent was removed under vacuum to afford the title compound, MS: M/Z 144 (M+H), which was taken directly to the next step.

Workup

  1. customThe protecting group was removed
  2. customThe catalyst was removed by filtration
  3. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-6951515be11f4de0861d142d08929d2e
Source dataset
uspto-grants-1992_08
Patent number
US05137892

Reaction notes

Loading…