3-Methoxyphenol → (5R,7R)-7-(4-(3-(3-methoxyphenoxy)propyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2[CH2:20][CH2:19][C@@:13]3([NH:17][C:16](=[O:18])[O:15][CH2:14]3)[CH2:12]2)=[CH:7][CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:40][O:41][C:42]1[CH:43]=[C:44](O)[CH:45]=[CH:46][CH:47]=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>C1COCC1>[CH3:40][O:41][C:42]1[CH:47]=[C:46]([CH:45]=[CH:44][CH:43]=1)[O:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C@@H:11]2[CH2:20][CH2:19][C@@:13]3([NH:17][C:16](=[O:18])[O:15][CH2:14]3)[CH2:12]2)=[CH:9][CH:10]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (5R,7R)-7-(4-(3-hydroxypropyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one (5.2 g, 18.89 mmol) in THF (150 mL) was added PS-triphenylphosphine 3 mmol/g (7.43 g, 28.3 mmol) followed by 3-methoxyphenol (2.457 mL, 22.66 mmol). After about 10 minutes a solution of di-tert-butylazodicarboxylate (5.22 g, 22.66 mmol) in THF (10 mL) was added. After about 4 hours the reaction mixture was filtered, rinsing with DCM and EtOAc. The filtrate was concentrated in vacuo and purified by chromatography on silica gel (DCM/EtOAc) to provide (5R,7R)-7-(4-(3-(3-methoxyphenoxy)propyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one (5.1 g, 13.37 mmol, 70.8% yield) as a colorless solid.
Workup
- filtrationAfter about 4 hours the reaction mixture was filtered
- washrinsing with DCM and EtOAc
- concentrationThe filtrate was concentrated in vacuo
- custompurified by chromatography on silica gel (DCM/EtOAc)
Sources & evidence
- ORD record
- ord-0fb7772c3a1e44f7b5b775fa3a48aa5c
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08217027B2
Reaction notes
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