Potassium Cyanide → (3aRS,4RS,6RS,7aSR)-6-cyanomethyl-4-(2-methoxyphenyl)-2-tert-butyloxycarbonylperhydroisoindol-4-ol

HRID 1599133Notes

Reaction equation

HRID 1599133 reaction equation
[C-:1]#[N:2].[K+].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1([OH:40])[CH2:20][CH:19]([CH2:21]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:18][CH:17]2[CH:13]1[CH2:14][N:15]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:16]2>CS(C)=O.O>[C:1]([CH2:21][CH:19]1[CH2:18][CH:17]2[CH:13]([CH2:14][N:15]([C:33]([O:35][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:34])[CH2:16]2)[C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH3:4])([OH:40])[CH2:20]1)#[N:2]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 18931539(3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-tert-butyloxycarbonyl-6-tosyloxymethylperhydroisoindol-4-ol

Product 1

HCID 18931585(3aRS,4RS,6RS,7aSR)-6-cyanomethyl-4-(2-methoxyphenyl)-2-tert-butyloxycarbonylperhydroisoindol-4-olYield 90.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

40 g of potassium cyanide are added carefully to a solution of 215 g of (3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-tert-butyloxycarbonyl-6-tosyloxymethylperhydroisoindol-4-ol in 800 cm3 of dimethyl sulphoxide. The reaction mixture is stirred at 50° C. for 20 hours, diluted with 1 liter of water and extracted with twice 200 cm3 and then 100 cm3 of ethyl acetate. The combined organic extracts are washed with twice 500 cm3 of water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is recrystallized from 200 cm3 of ethyl ether, and the crystals are washed with the same solvent, drained and then dried under reduced pressure (2.7 kPa). 142 g of (3aRS,4RS,6RS,7aSR)-6-cyanomethyl-4-(2-methoxyphenyl)-2-tert-butyloxycarbonylperhydroisoindol-4-ol are obtained in the form of a white solid. M.p.K =149° C.

Workup

  1. extractionextracted with twice 200 cm3
  2. washThe combined organic extracts are washed with twice 500 cm3 of water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue obtained
  6. customis recrystallized from 200 cm3 of ethyl ether
  7. washthe crystals are washed with the same solvent
  8. customdried under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-13e07315dfb7455d8a22eb924572f089
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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