Diethyl Ether → Boron trifluoride etherate

HRID 749400Notes

Reaction equation

C1C[C@H]2N(C[C@H]3[C@@H]4CCCCN4C[C@@H]2C3)CC1.[Li]C(CC)C.[B:23]([F:26])([F:25])[F:24].[CH3:27][CH2:28][O:29][CH2:30][CH3:31]>>[B:23]([F:26])([F:25])[F:24].[CH3:27][CH2:28][O:29][CH2:30][CH3:31]

Participants

Reactant 4

HCID 3283Diethyl Ether

HCID 6356Boron trifluoride

HCID 644020Sparteine

HCID 178418400CID 53628100

Product 1

HCID 8000Boron trifluoride etherateYield 83%

Procedure

Scheme 4 provides an example of an embodiment of the process shown in Scheme 3. In this particular embodiment, the chiral diamine is (−)-sparteine, the organometallic compound is an organolithium compound, and more concretely it is s-BuLi, the solvent is Et2O, the strained cyclic ether is the epoxide ethylene oxide, the Lewis acid is BF3, provided as BF3.Et2O, m=1, and n=3. A compound of formula (Ia) in Scheme 4 can be characterized as being the enantiomer (+)-(R) because it is obtained in an ee of at least 80%, and in some embodiments about 82%. A compound of formula (Ia) was obtained in embodiments of this invention with a yield of about 83% and ee of about 82%.

Workup

customScheme 4 provides an example of an embodiment of the process

Sources & evidence

ORD record: ord-9b78f1bd0be94444845d51c5656e9672
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402670B2

Reaction notes

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