Isopropanol → HCID 67178003, compound

HRID 885155Notes

Reaction equation

HRID 885155 reaction equation
[CH3:1][C:2]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:16])[CH2:3][CH2:4]/[CH:5]=[N:6]/[S@:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=[O:8].[C-:23]#[N:24].C([Al+]CC)C.C(O)(C)C.[Cl-].[NH4+]>O1CCCC1>[C:23]([C@@H:5]([NH:6][S@:7]([C:9]1[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1)=[O:8])[CH2:4][CH2:3][C:2]([CH3:1])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])#[N:24]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 25517Ammonium ChlorideHCID 16686413Diethyl aluminum cyanideHCID 87317008HCID 87317008, compound

Product 1

HCID 67178003HCID 67178003, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

(S)-4-methyl-benzenesulfinic acid [4-methyl-4-phenyl-pent-(E)-ylidene]-amide (1.29 g) was dissolved in tetrahydrofuran (35 ml) and cooled to −78° C. In a second flask diethylaluminium cyanide solution (1N in toluene, 9.5 ml) was diluted with tetrahydrofuran (35 ml). After cooling down to −78° C. isopropanol (0.31 ml) was added and the mixture was stirred additional 30 min at room temperature. This mixture was added slowly to the imine solution in the first flask at −78° C. and stirred overnight while warming up to room temperature. After cooling down to −78° C. saturated ammonium chloride solution (18 ml) was added. The suspension was filtered through Celite. Ethyl acetate was added and the solution was washed with sodium chloride solution, dried (MgSO4) and concentrated. The crude product was purified by column chromatography (SiO2; heptane/EtOAc 4:1) to give (S)-4-methyl-benzenesulfinic acid ((S)-1-cyano-4-methyl-4-phenyl-pentyl)-amide (0.6 g, 43%) as a light yellow oil.

Workup

  1. additionwas added
  2. stirringstirred overnight
  3. temperaturewhile warming up to room temperature
  4. additionwas added
  5. filtrationThe suspension was filtered through Celite
  6. additionEthyl acetate was added
  7. washthe solution was washed with sodium chloride solution
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe crude product was purified by column chromatography (SiO2; heptane/EtOAc 4:1)

Sources & evidence

ORD record
ord-640be5547708424281a40c49c28d3325
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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