N-Fluorobenzenesulfonimide → HCID 69105402, compound

HRID 2224051Notes

Reaction equation

HRID 2224051 reaction equation
C([Li])(CC)C.[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][C:13]1[CH:30]=[CH:29][C:28]2[C@@H:27]3[C@:18]([CH:38]=[CH2:39])([C@H:19]4[C@@:23]([CH2:25][CH2:26]3)([CH3:24])[C@@H:22]([O:31][CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)[CH2:21][CH2:20]4)[CH2:17][CH2:16][C:15]=2[CH:14]=1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:50])(=O)=O)=CC=1>C1COCC1>[F:50][C:30]1[C:13]([O:12][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:6]2)=[CH:14][C:15]2[CH2:16][CH2:17][C@:18]3([CH:38]=[CH2:39])[C@@H:27]([C:28]=2[CH:29]=1)[CH2:26][CH2:25][C@@:23]1([CH3:24])[C@H:19]3[CH2:20][CH2:21][C@@H:22]1[O:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][O:33]1

Participants

5

Reactant 3

HCID 588007N-FluorobenzenesulfonimideHCID 69104899HCID 69104899, compoundHCID 178418400CID 53628100

Product 1

HCID 69105402HCID 69105402, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

3 ml of a 1.3 M s-butyllithium solution was added in drops under argon to a solution of 120 mg of 3,17β-bis-(tetrahydropyran-2-yloxy)-8β-vinyl-estra-1,3,5(10)-triene in 4 ml of THF that was cooled to −78° C., it was stirred for 30 minutes and then a solution that consists of 650 mg of N-fluorodibenzenesulfonimide in 4 ml of THF was added in drops while being exposed to continuous cooling. The reaction mixture was stirred first for 1 hour at −78° C. then for another 16 hours while being heated to room temperature. The reaction solution was poured onto ice water, extracted several times with ethyl acetate, the collected organic phases were washed with saturated sodium chloride solution, dried on magnesium sulfate and concentrated by evaporation in a vacuum. The dark, oily crude product (330 mg) was used in the next stage without further purification.

Workup

  1. additionwas added in drops
  2. stirringThe reaction mixture was stirred first for 1 hour at −78° C.
  3. temperaturefor another 16 hours while being heated to room temperature
  4. additionThe reaction solution was poured onto ice water
  5. extractionextracted several times with ethyl acetate
  6. washthe collected organic phases were washed with saturated sodium chloride solution
  7. customdried on magnesium sulfate
  8. concentrationconcentrated by evaporation in a vacuum
  9. customThe dark, oily crude product (330 mg) was used in the next stage without further purification

Sources & evidence

ORD record
ord-c3b258172be6432eaef63d79cf935ec0
Source dataset
uspto-grants-2008_05
Patent number
US07378404B2

Reaction notes

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