Boron trifluoride etherate → HCID 86620048, compound

HRID 1993982Notes

Reaction equation

HRID 1993982 reaction equation
[N+](C1C=CC(C(O[CH:11]2[CH:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])[CH:15]([CH2:25][O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:14]([CH2:34][O:35][C:36](=[O:46])[C:37]3[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][CH:38]=3)[CH2:13][O:12]2)=O)=CC=1)([O-])=O.[F:49][C:50]([F:65])([F:64])[C:51]1[CH:52]=[C:53]([C@H:61]([OH:63])[CH3:62])[CH:54]=[C:55]([C:57]([F:60])([F:59])[F:58])[CH:56]=1.B(F)(F)F.CCOCC>C(Cl)Cl>[N+:43]([C:40]1[CH:41]=[CH:42][C:37]([C:36]([O:35][CH2:34][C@@H:14]2[C@@H:15]([CH2:25][O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])[C@@H:11]([O:63][C@@H:61]([C:53]3[CH:52]=[C:51]([C:50]([F:64])([F:65])[F:49])[CH:56]=[C:55]([C:57]([F:58])([F:59])[F:60])[CH:54]=3)[CH3:62])[O:12][CH2:13]2)=[O:46])=[CH:38][CH:39]=1)([O-:45])=[O:44]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 2779031(alphaR)-alpha-Methyl-3,5-bis(trifluoromethyl)benzenemethanolHCID 86620049HCID 86620049, compound

Product 1

HCID 86620048HCID 86620048, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-25 °C

Procedure

The intermediate from step F (6.17 g, 9.36 mmol) was combined with (1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethanol (2.53 g, 9.83 mmol) and dissolved in 100 mL DCM. The vessel was cooled to −25° C. followed by the addition boron trifluoride etherate (0.23 mL, 1.87 mmol). The reaction vessel was maintained at −25° C. for 1 hr. The reaction was quenched by the addition of a saturated solution of NaHCO3 and the mixture was allowed to warm to ambient temperature. The aqueous mixture was extracted several times with EtOAc and washed with brine, dried over Na2SO4, filtered through a fritted funnel and concentrated in vacuo. The crude residue was purified on silica gel and eluted with tBuOMe/hexanes=10 to 14%. The first component collected off the column was the desired diastereomer. (M+Na)+772

Workup

  1. temperatureThe reaction vessel was maintained at −25° C. for 1 hr
  2. customThe reaction was quenched by the addition of a saturated solution of NaHCO3
  3. temperatureto warm to ambient temperature
  4. extractionThe aqueous mixture was extracted several times with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered through a fritted funnel
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified on silica gel
  10. washeluted with tBuOMe/hexanes=10 to 14%
  11. customThe first component collected off the column

Sources & evidence

ORD record
ord-6cc3309f757a4af0ad0181254a143837
Source dataset
uspto-grants-2010_01
Patent number
US07652058B2

Reaction notes

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