Tetrahydrofuran → 2-[3-(2,2-Dimethylpropanoyl)-6-phenyl-1,3-oxazinan-6-yl]ethanol
Reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:16][CH2:15][N:14]([C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:13][CH2:12]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.C([O-])(O)=O.[Na+]>>[CH3:19][C:18]([CH3:21])([CH3:20])[C:17]([N:14]1[CH2:13][CH2:12][C:11]([CH2:10][CH2:9][OH:8])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:16][CH2:15]1)=[O:22]Participants
Procedure
6-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-(2,2-dimethylpropanoyl)-6-phenyl-1,3-oxazinane (4.07 g, 10.03 mmol) was stirred in a 1M solution of tetrabutylammonium fluoride in THF (40 mL, 40 mmol) for 2 h at room temperature. Saturated aqueous NaHCO3 was added, and the reaction mixture was extracted with CHCl3. The organic layers were dried (Na2SO4), concentrated and the residue was filtered through a silica plug flushing with 1:1 hex:EtOAc to afford 2-[3-(2,2-dimethylpropanoyl)-6-phenyl-1,3-oxazinan-6-yl]ethanol in quantitative yield as a clear oil that was used without further purification. 1H NMR (400 MHz, CDCl3): δ 37.45-7.37 (m, 4H), 7.31 (m, 1H), 5.51 (dd, 1H, J=10.9, 2.1 Hz), 4.69 (d, 1H, J=11.0 Hz), 4.30 (m, 1H), 3.58 (m, 2H), 2.99 (m, 1H), 2.31 (dt, 1H, J=14.1, 3.4 Hz), 2.16 (ddd, 1H, J=14.1, 11.7, 4.4 Hz), 2.04 (ddd, 1H, J=14.5, 7.0, 4.7 Hz), 1.92 (ddd, 1H, J=14.6, 6.9, 4.7 Hz), 1.28 (s, 9H).
Workup
- extractionthe reaction mixture was extracted with CHCl3
- dry with materialThe organic layers were dried (Na2SO4)
- concentrationconcentrated
- filtrationthe residue was filtered through a silica plug
- customflushing with 1:1 hex
Sources & evidence
- ORD record
- ord-e1e9d670ae2e41bfa58292c73c3ff94d
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07452992B2
Reaction notes
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