(Diethylamino)sulfur trifluoride → HCID 10282769, compound

HRID 1532980Notes

Reaction equation

HRID 1532980 reaction equation
C(N(S(F)(F)[F:7])CC)C.[Si:10]([O:17][CH:18]1[CH2:27][C:26]([CH3:29])([CH3:28])[CH2:25][C:24]2[N:23]=[C:22]([CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[C:21]([CH:35]([C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=3)O)=[C:20]([C:47]3[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=3)[C:19]1=2)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>C1(C)C=CC=CC=1>[Si:10]([O:17][CH:18]1[CH2:27][C:26]([CH3:29])([CH3:28])[CH2:25][C:24]2[N:23]=[C:22]([CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[C:21]([CH:35]([F:7])[C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:45])([F:44])[F:46])=[CH:39][CH:38]=3)=[C:20]([C:47]3[CH:48]=[CH:49][C:50]([F:53])=[CH:51][CH:52]=3)[C:19]1=2)([C:13]([CH3:14])([CH3:15])[CH3:16])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 10145895HCID 10145895, compound

Product 1

HCID 10282769HCID 10282769, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1.46 g of diethylaminosulphur trifluoride dissolved in 10 ml of toluene were added dropwise at −5° C. to 3.8 g of [5-(tert-butyldimethylsilanyloxy)-2-cyclopentyl-4-(4-fluorophenyl)-7,7-dimethyl-5,6,7, 8-tetrahydroquinolin-3-yl]-(4-trifluoromethylphenyl)-methanol dissolved in 37.8 ml of toluene. The reaction was quenched after 30 minutes using saturated aqueous sodium hydrogencarbonate solution and the organic phase was washed again using saturated aqueous sodium hydrogencarbonate solution and dried. After distilling off the solvent in vacuo, the residue was recrystallized from ethanol. A total of 3.33 g of colorless crystals having a purity of 99.4% according to HPLC resulted. By chromatography on silica gel, it was possible from the mother liquor of the crystallization, using petroleum ether/ethyl acetate 10:1, to obtain a further 0.26 g of the same quality.

Workup

  1. customThe reaction was quenched after 30 minutes
  2. washthe organic phase was washed again using saturated aqueous sodium hydrogencarbonate solution
  3. customdried
  4. distillationAfter distilling off the solvent in vacuo
  5. customthe residue was recrystallized from ethanol
  6. customresulted
  7. customBy chromatography on silica gel, it was possible from the mother liquor of the crystallization
  8. customto obtain a further 0.26 g of the same quality

Sources & evidence

ORD record
ord-0f38b2aa0646497d8957ca32f02fc3eb
Source dataset
uspto-grants-2001_03
Patent number
US06207671B1

Reaction notes

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