Triphenylphosphine → Tert-butyl 4-(2-(ethylthio)quinazolin-7-yloxy)piperidine-1-carboxylate
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].[CH2:34]([S:36][C:37]1[N:46]=[CH:45][C:44]2[C:39](=[CH:40][C:41](O)=[CH:42][CH:43]=2)[N:38]=1)[CH3:35]>C1COCC1>[CH2:34]([S:36][C:37]1[N:46]=[CH:45][C:44]2[C:39](=[CH:40][C:41]([O:33][CH:30]3[CH2:31][CH2:32][N:27]([C:25]([O:24][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:26])[CH2:28][CH2:29]3)=[CH:42][CH:43]=2)[N:38]=1)[CH3:35]Participants
5
Procedure
To a solution of triphenylphosphine (2 eq) in THF was added di-terbutylazodicarboxylate (2 eq). The mixture was stirred 15 minutes at ambient temperature under nitrogen atmosphere. To that was added tert-butyl-4-hydroxypiperidine-1-carboxylate (5 eq). The mixture was stirred 15 minutes at ambient temperature followed by addition of 2-(ethylthio) quinazolin-7-ol (1 eq). The mixture was stirred overnight at ambient temperature. The reaction mixture was concentrated and purified by flash column chromatography (10% EtOAc/Hexane) to provide product as a white solid in 90% yield. ES/MS m/z 390.1 (MH+).
Workup
- stirringThe mixture was stirred 15 minutes at ambient temperature
- stirringThe mixture was stirred overnight at ambient temperature
- concentrationThe reaction mixture was concentrated
- custompurified by flash column chromatography (10% EtOAc/Hexane)
- customto provide product as a white solid in 90% yield
Sources & evidence
- ORD record
- ord-ce4eee9a0cee4e84bfbff6469135e045
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932262B2
Reaction notes
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