1,5-Dioxa-8-azaspiro[5.4]decane benzyl carbamate → 6,10-Dioxa-2-azaspiro[4.5]decane
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]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- customThe protecting group was removed
- customThe catalyst was removed by filtration
- customthe solvent was removed under vacuum
Sources & evidence
- ORD record
- ord-6951515be11f4de0861d142d08929d2e
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05137892
Reaction notes
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