Sodium sulfate decahydrate → (S)-1,1,1-trifluoro-2-(1-{[4-(4-fluorophenyl)-2-(1-hydroxyethyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)butan-2-ol

HRID 2422563Notes

Reaction equation

HRID 2422563 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][N:19]4[CH:23]=[C:22]([C@:24]([OH:31])([C:27]([F:30])([F:29])[F:28])[CH2:25][CH3:26])[N:21]=[N:20]4)=[CH:15][CH:16]=3)[N:11]=[C:10]([C:32](=[O:34])[CH3:33])[CH:9]=2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>ClCCl.CC(C)=O>[F:30][C:27]([F:28])([F:29])[C@:24]([C:22]1[N:21]=[N:20][N:19]([CH2:18][C:14]2[CH:13]=[C:12]3[C:17]([C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[CH:9][C:10]([CH:32]([OH:34])[CH3:33])=[N:11]3)=[CH:16][CH:15]=2)[CH:23]=1)([OH:31])[CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21225700DiisobutylaluminumhydrideHCID 66790923(S)-1-[4-(4-fluorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinolin-2-yl]ethanone

Product 1

HCID 66791197(S)-1,1,1-trifluoro-2-(1-{[4-(4-fluorophenyl)-2-(1-hydroxyethyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)butan-2-ol

Reagents, catalysts & solvents 2

HCID 180AcetoneCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1-[4-(4-fluorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinolin-2-yl]ethanone (100 mg, 0.21 mmol) in dichloromethane (5 mL) at −78° C. was added diisobutylaluminum hydride (79 μL, 0.44 mmole). The solution was stirred 20 minutes after which a few drops of acetone were added. The reaction was warmed up to rt and sodium sulfate decahydrate (205 mg, 0.63 mmol) was added. After stirring for 30 minutes the mixture was filtered on celite and concentrated. Purification on silica gel (eluting with acetone/dichloromethane, 3:7) gave the title compound. MS (+ESI): 475 (M+H)+.

Workup

  1. additionwere added
  2. filtrationwas filtered on celite and
  3. concentrationconcentrated
  4. customPurification on silica gel (eluting with acetone/dichloromethane, 3:7)

Sources & evidence

ORD record
ord-489769b6419740d0a2c5276f5aaab99d
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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