Boron trifluoride etherate → HCID 58468278, compound

HRID 2094646Notes

Reaction equation

HRID 2094646 reaction equation
B(F)(F)F.CCOCC.[F:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21](O)([C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[C@@H:22]([C:26]2[CH:38]=[CH:37][C:29]([C:30]([O:32]C(C)(C)C)=[O:31])=[CH:28][CH:27]=2)[CH2:23][CH2:24][CH3:25])=[CH:13][CH:12]=1>C(Cl)Cl.CCOC(C)=O>[F:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH:21]([C:39]2[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=2)[C@@H:22]([C:26]2[CH:38]=[CH:37][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=2)[CH2:23][CH2:24][CH3:25])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 8000Boron trifluoride etherateHCID 58468275HCID 58468275, compound

Product 1

HCID 58468278HCID 58468278, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Boron trifluoride diethyl etherate (0.074 mL, 0.583 mmol) was added dropwise to a solution of tert-butyl 4-{(1R)-1-[(4-fluoro-1-naphthyl)(hydroxy)(4-methoxyphenyl)methyl]butyl}benzoate (150 mg, 0.291 mmol) in DCM (2 mL) at 0° C. The solution was allowed to warm to RT and stirred overnight. The solution was diluted with EtOAc (30 mL) then washed with water and brine. The organic layer was dried over MgSO4, filtered, then concentrated to provide the title compound which was used directly in the next step without further purification. LC1 1.20 min. [M+H]+ 442.

Workup

  1. washthen washed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3d580d82898445259befc4b0298e025f
Source dataset
uspto-grants-2013_05
Patent number
US08445538B2

Reaction notes

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