Water → Triapenthenol

HRID 1709739Notes

Reaction equation

HRID 1709739 reaction equation
B([O-])=O.[Na+].[CH:5]1([CH:11]=[C:12]([N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.O>O1CCCC1>[CH:5]1(/[CH:11]=[C:12](/[N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)\[CH:13]([OH:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 145326Sodium metaborateHCID 566097071-Cyclohexyl-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one

Product 1

HCID 6437842Triapenthenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.68 g (0.018 mol) of sodium boranate is added to a suspension of 5.2 g (0.018 mol) of S-2-(dibenzyl-hydroxymethyl)-pyrrolidine hydrochloride in 75 ml of absolute tetrahydrofuran at -30° C., with stirring. The temperature is allowed to rise gradually to 20° C. and stirring is continued at 20° C. for a further 2 hours. Thereafter, 3.15 g (0.012 mol) of the (E)-isomer of 1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-one are added dropwise and the mixture is stirred at 40° C. for 20 hours. The reaction mixture is then poured into water. The resulting mixture is extracted with ethyl acetate and the combined organic phases are concentrated under reduced pressure. The residue which remains is chromatographed with a mixture of chloroform/ethyl acetate=4:1 on silica gel. 2.1 g (67% of theory) of the (-)-antipode of (E)-1-cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ene are obtained in this manner in the form of a crystalline product.

Workup

  1. customto rise gradually to 20° C.
  2. stirringstirring
  3. stirringthe mixture is stirred at 40° C. for 20 hours
  4. extractionThe resulting mixture is extracted with ethyl acetate
  5. concentrationthe combined organic phases are concentrated under reduced pressure
  6. customThe residue which remains is chromatographed with a mixture of chloroform/ethyl acetate=4:1 on silica gel

Sources & evidence

ORD record
ord-23f8f4fe2e884839a33a613e03f3e5de
Source dataset
uspto-grants-1990_08
Patent number
US04950767

Reaction notes

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