(Diethylamino)sulfur trifluoride → HCID 22481031, compound

HRID 1596334Notes

Reaction equation

HRID 1596334 reaction equation
C(N(S(F)(F)[F:7])CC)C.[C:10]([Si:14]([CH3:54])([CH3:53])[O:15][CH:16]1[CH2:25][C:24]([CH3:27])([CH3:26])[CH2:23][C:22]2[N:21]=[C:20]([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[C:19]([CH:33]([C:35]3[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=3)O)=[C:18]([C:45]3[CH:50]=[CH:49][C:48]([F:51])=[C:47]([F:52])[CH:46]=3)[C:17]1=2)([CH3:13])([CH3:12])[CH3:11]>C1(C)C=CC=CC=1>[Si:14]([O:15][CH:16]1[CH2:25][C:24]([CH3:26])([CH3:27])[CH2:23][C:22]2[N:21]=[C:20]([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[C:19]([CH:33]([F:7])[C:35]3[CH:36]=[CH:37][C:38]([C:41]([F:44])([F:42])[F:43])=[CH:39][CH:40]=3)=[C:18]([C:45]3[CH:50]=[CH:49][C:48]([F:51])=[C:47]([F:52])[CH:46]=3)[C:17]1=2)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:54])[CH3:53]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 22481034HCID 22481034, compound

Product 1

HCID 22481031HCID 22481031, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

At −5° C., 0.06 ml of diethylaminosulphur trifluoride, dissolved in 10.15 ml of toluene, was added dropwise to 200 mg (0.3 mmol) of [5-(tertbutyldimethylsilanyloxy)-2-cyclopentyl-4-(3,4-difluorophenyl)-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl]-(4-trifluoromethylphenyl)-methanol dissolved in 2 ml of toluene. After 60 minutes, the reaction was quenched with saturated aqueous sodium bicarbonate solution, toluene was added and the organic phase was washed once more with saturated aqueous sodium bicarbonate solution and dried. The solvent was distilled off under reduced pressure and the residue was then purified over a silica gel column This gave a total of 190 mg of a colourless oil.

Workup

  1. customthe reaction was quenched with saturated aqueous sodium bicarbonate solution, toluene
  2. additionwas added
  3. washthe organic phase was washed once more with saturated aqueous sodium bicarbonate solution
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was then purified over a silica gel column

Sources & evidence

ORD record
ord-0c936a7a48f14de794a91f207ea487b7
Source dataset
uspto-grants-2001_09
Patent number
US06291477B1

Reaction notes

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