Sodium Bicarbonate → HCID 68665485, compound

HRID 1443412Notes

Reaction equation

HRID 1443412 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][C@H:10](O)[CH2:9]2)=[CH:4][CH:3]=1.COCCN(S(F)(F)[F:24])CCOC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][C@@H:10]([F:24])[CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 68666066HCID 68666066, compound

Product 1

HCID 68665485HCID 68665485, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S,3R)-3-(4-bromophenyl)cyclopentanol (503 mg, 2.09 mmol) in 10 mL of CH2Cl2 at −78° C. was added (bis(2-methoxyethyl)amino)sulfur tri fluoride (Deoxo-Fluor, 462 μL, 2.50 mmol). The mixture was allowed to gradually warm up to rt overnight and then poured into sat'd NaHCO3 (20 mL). The aqueous layer was extracted with CH2Cl2 (3×20 mL). The organic layer was dried over MgSO4 and concentrated. Chromatography on a Biotage 40+S cartridge using hexanes as the eluant afforded 383 mg (76%) of the title compound: 1H NMR δ 1.53-1.78 (m, 2H), 1.95-2.39 (m, 4H), 3.35 (m, 1H), 5.19-5.32 (m, 1H), 7.09 (d, J 8.5, 2H), 7.40 (d, J=8.2, 2H).

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-23ba668a8543498bb5455f243fd134c5
Source dataset
uspto-grants-2010_02
Patent number
US07659294B2

Reaction notes

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