Water → HCID 53906647, compound

HRID 654873Notes

Reaction equation

HRID 654873 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][C@H:20]([CH:40]([OH:42])[CH3:41])[C@:21]([C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)([O:28][Si](C)(C)C)[CH2:22][N:23]1[CH:27]=[N:26][CH:25]=[N:24]1.O>O1CCCC1>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([C@:21]([OH:28])([C@H:20]([CH3:19])[CH:40]([OH:42])[CH3:41])[CH2:22][N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 15008635HCID 15008635, compound

Product 1

HCID 53906647HCID 53906647, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.35 ml (0.35 mmole) of tetrabutylammonium fluoride (as a 1 molar tetrahydrofuran solution) was added to a solution of 85.4 mg (0.233 mmole) of (2R*,3R*)-3-methyl-2-(4-chlorophenyl)-2-(trimethylsilyloxy)-1-(1H-1,2,4-triazol -1-yl)-4-pentanol (prepared as described in Preparation 7) in 2.5 ml of tetrahydrofuran, and then the mixture was stirred at room temperature for 30 minutes. At the end of this time, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to afford 64 mg (93%) of the title compound. Judging from the NMR spectrum, this compound is thought to be about a 5:1 mixture of the (2R*,3R*,4S*) isomer and the (2R*,3R*,4R*) isomer.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-9a0316a5177e4c9d9fab0e7c40829901
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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