Boron trifluoride etherate → HCID 71078475, compound

HRID 576414Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:4][C:5]([C:11]2(OC)[C@H:16]([OH:17])[C@@H:15]([OH:18])[C@H:14]([OH:19])[C@@H:13]([CH2:20][OH:21])[O:12]2)=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl.CC#N>[Br:1][C:2]1[C:3]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)=[CH:4][C:5]([C@H:11]2[C@H:16]([OH:17])[C@@H:15]([OH:18])[C@H:14]([OH:19])[C@@H:13]([CH2:20][OH:21])[O:12]2)=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2

Participants

Conditions

Temperature: -30 °C

Procedure

To a solution of compound 15 (0.94 g, 1.85 mmol) in CH2Cl2/CH3CN (8.9 mL/8.9 mL) were added triethylsilane (0.59 mL, 3.7 mmol) and boron trifluoride diethyl etherate (0.46 mL, 3.7 mmol) at −60° C. under nitrogen atmosphere. The mixture was warmed up to −30° C. for 2 h. The reaction mixture was quenched with saturated NaHCO3 solution (15 mL) and extracted with EtOAc (50 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by prep HPLC (reverse phase) to provide the compound E001 (0.15 g, 0.306 mmol, 17%).

Workup

customThe reaction mixture was quenched with saturated NaHCO3 solution (15 mL)
extractionextracted with EtOAc (50 mL)
washThe organic layer was washed with brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by prep HPLC (reverse phase)
customto provide the compound E001 (0.15 g, 0.306 mmol, 17%)

Sources & evidence

ORD record: ord-0b01d508d8814603a45f03806b343cbf
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034921B2

Reaction notes

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