(5R,7R)-7-(4-(3-(benzyloxy)prop-1-ynyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one → (5R,7R)-7-(4-(3-hydroxypropyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one
Reaction equation
C([O:8][CH2:9][C:10]#[C:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]2[CH2:27][CH2:26][C@@:20]3([NH:24][C:23](=[O:25])[O:22][CH2:21]3)[CH2:19]2)=[CH:14][CH:13]=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[OH:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C@@H:18]2[CH2:27][CH2:26][C@@:20]3([NH:24][C:23](=[O:25])[O:22][CH2:21]3)[CH2:19]2)=[CH:16][CH:17]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of palladium hydroxide on carbon (0.583 g, 0.830 mmol) in MeOH (250 mL) was added a solution of (5R,7R)-7-(4-(3-(benzyloxy)prop-1-ynyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one (20 g, 41.5 mmol) in MeOH (10 mL). Hydrogen was bubbled through the solution for about 10 minutes and an atmosphere of hydrogen was maintained via balloon. After about 15 hours the reaction mixture was filtered through Celite® and concentrated in vacuo. The crude product was purified by chromatography on silica gel (EtOAc/DCM) to provide (5R,7R)-7-(4-(3-hydroxypropyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one (5.2 g, 18.89 mmol, 45.5% yield) as a colorless solid.
Workup
- customHydrogen was bubbled through the solution for about 10 minutes
- temperaturean atmosphere of hydrogen was maintained via balloon
- filtrationAfter about 15 hours the reaction mixture was filtered through Celite®
- concentrationconcentrated in vacuo
- customThe crude product was purified by chromatography on silica gel (EtOAc/DCM)
Sources & evidence
- ORD record
- ord-8b3eea31fe484b38a89d4a2b71015eb4
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08217027B2
Reaction notes
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