Tetrahydrofuran → HCID 22624689, compound

HRID 279357Notes

Reaction equation

HRID 279357 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH2:11][CH2:10][CH:9]([CH:12]([CH3:21])[CH2:13][NH:14][S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[CH2:8][CH:7]=1.[O:22]1CCCC1>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]([CH3:21])[CH2:13][NH:14][S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[CH2:8][CH:7]1[OH:22]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 9905470HCID 9905470, compound

Product 1

HCID 22624689HCID 22624689, compound

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 1 eq. of N-[2-[4-(2-thienyl)-3-cyclohexen-1-yl]propyl] 2-propanesulfonamide (see example 8) in tetrahydrofuran is added 0.67 eq. of borane dimethyl sulfide complex. The mixture is stirred at 0° C. for 4 hr and slowly quenched with ethanol. To the 0° C. solution is added 3N aqueous sodium hydroxide then 30% aqueous hydrogen peroxide. The mixture is stirred at 0° C. for one hr. The organic portion is separated and the aqueous portion is extracted two times with diethyl ether. The combined organic extracts are dried over MgSO4, filtered and concentrate in vacuo to provide the crude material. Chromatography (silica gel) of the crude material affords the purified title compound.

Workup

  1. customslowly quenched with ethanol
  2. additionTo the 0° C. solution is added 3N aqueous sodium hydroxide
  3. stirringThe mixture is stirred at 0° C. for one hr
  4. customThe organic portion is separated
  5. extractionthe aqueous portion is extracted two times with diethyl ether
  6. dry with materialThe combined organic extracts are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrate in vacuo
  9. customto provide the crude material

Sources & evidence

ORD record
ord-51ccee806c694fd0901f1b0cdabb5bef
Source dataset
uspto-grants-2002_03
Patent number
US06362230B1

Reaction notes

Loading…