Carbon Dioxide → HCID 11701359, compound

HRID 1443410Notes

Reaction equation

HRID 1443410 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][C:10]([F:14])([F:13])[CH2:9]2)=[CH:4][CH:3]=1.[Li]CCCC.[C:20](=[O:22])=[O:21]>C1COCC1.CCOCC>[F:13][C:10]1([F:14])[CH2:11][CH2:12][C@@H:8]([C:5]2[CH:6]=[CH:7][C:2]([C:20]([OH:22])=[O:21])=[CH:3][CH:4]=2)[CH2:9]1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 68666112HCID 68666112, compoundHCID 178418339Butyllithium

Product 1

HCID 11701359HCID 11701359, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.0 g (3.8 mmol) of (R)-3-(4-bromophenyl)-1,1-difluorocyclopentane (from Step B) in 15 mL of THF at −78° C. was treated with 1.6 mL (4.0 mmol) of 2.5M BuLi in hexanes. After stirring for 15 min, the reaction mixture was added to a suspension of dry ice in 200 mL of Et2O. The mixture was allowed to warm to rt. The reaction mixture was extracted with 100 mL of 1 N NaOH. After separating phases, the aqueous layer was acidified to pH 1-2 with concentrated HCl. The aqueous phase was extracted with 3×100 mL of CH2Cl2. The combined organic phases were dried and concentrated to give 0.67 g of the title compound: 1H NMR (CD3OD) δ 1.87 (m, 1H), 2.13-2.37 (m, 4H), 2.54 (m, 11H), 3.41 (m, 1H), 7.39 (d, J=8.2, 2H), 7.97 (d, J=8.2, 2H).

Workup

  1. extractionThe reaction mixture was extracted with 100 mL of 1 N NaOH
  2. customAfter separating phases
  3. extractionThe aqueous phase was extracted with 3×100 mL of CH2Cl2
  4. customThe combined organic phases were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-20fd0790557b46619ef7ad597a88e7b7
Source dataset
uspto-grants-2010_02
Patent number
US07659294B2

Reaction notes

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