Boron trifluoride etherate → HCID 66671642, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[CH:9]1[CH2:14][CH2:15][C:16](OCC)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].B(F)(F)F.CCOCC.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[CH:9]1[CH:14]=[CH:15][CH2:16][OH:17])=[O:7])([CH3:2])([CH3:4])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution containing crude 61 (16.7 g, 0.059 mol) in DCM (150 mL) was cooled to −78° C. BF3.Et2O (8.9 mL, 0.07 mol) was added followed by the dropwise addition of DIBAL (2 M/DCM, 200 mL, 0.4 mol). After 2 h, TLC analysis indicated complete consumption of the 61 [TLC analysis: 1:1 hexane/EtOAc, Rf(62)=0.3]. EtOAc (40 mL) was added and the reaction mixture was warmed to −15° C. The reaction mixture was carefully quenched with 1M HCl until pH=2. The product was extracted with DCM. The organic extracts were washed with 1M HCl, water, and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude 62 was purified by silica gel chromatography (2:1 hexanes/EtOAc) to afford 7.2 g (51%) of 62. 1H NMR (CDCl3, 300 MHz) δ5.8-5.5 (m, 2H), 4.18 (m, 2H), 4.0-3.25 (m, 3H), 2.2-1.85 (m, 2H), 1.55-1.3 (m. 1H), 1.43 (s, 9H), 1.15 (d, J=6 Hz, 3H) ppm.
Workup
- customconsumption of the 61 [TLC analysis
- additionEtOAc (40 mL) was added
- temperaturethe reaction mixture was warmed to −15° C
- customThe reaction mixture was carefully quenched with 1M HCl until pH=2
- extractionThe product was extracted with DCM
- washThe organic extracts were washed with 1M HCl, water, and brine
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude 62 was purified by silica gel chromatography (2:1 hexanes/EtOAc)
Sources & evidence
- ORD record
- ord-97d455a1d0f04acca4349234b3e978cc
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07985735B2
Reaction notes
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