HCID 69663378, compound → HCID 69662332, compound

HRID 2212073Notes

Reaction equation

HRID 2212073 reaction equation
C([Li])CCC.[C:6]1([S:12]([C@H:15]([CH3:21])[C@H:16]([CH3:20])[CH2:17][CH2:18][OH:19])(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1>[C:6]1([S:12]([C@@H:15]([CH3:21])[C@H:16]([CH3:20])[CH2:17][CH2:18][OH:19])(=[O:13])=[O:14])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 69663378HCID 69663378, compoundHCID 178418339Butyllithium

Product 1

HCID 69662332HCID 69662332, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

n-Butyllithium in hexanes (0.165 ml, 0.25 mmol) was added dropwise to a stirred solution of (3R*,4R*)-4-benzenesulfonyl-3-methylpentan-1-ol (286 mg, 1.2 mmol) in THF (5 ml) at −78° C. The mixture was warmed to 0° C. over 30 min. and quenched with satd. aqueous NH4Cl and extracted with dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated to give a mixture syn:anti diastereoisomeric sulfones in a 6:1 ratio respectively.

Workup

  1. customquenched with satd
  2. extractionaqueous NH4Cl and extracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customto give a mixture syn

Sources & evidence

ORD record
ord-ea53e607d5964a968dfb66debd969106
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

Loading…