Hydrochloric Acid → (2S,4R)-4-p-toluenesulfonyloxy-2-(4-methoxyphenyl)-decanenitrile

HRID 973512Notes

Reaction equation

HRID 973512 reaction equation
[OH:1][C@H:2]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:3][C@@H:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[C:5]#[N:6].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.Cl>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([O:1][C@H:2]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:3][C@@H:4]([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=2)[C:5]#[N:6])(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 15653381(2S,4R)-4-hydroxy-2-(4-methoxyphenyl)decanenitrile

Product 1

HCID 15733980(2S,4R)-4-p-toluenesulfonyloxy-2-(4-methoxyphenyl)-decanenitrileYield 64%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Procedure

To a solution of 559 mg (2.0 mmol) of (2S,4R)-4-hydroxy-2-(4-methoxyphenyl)decanenitrile in 5 ml of pyridine were added, with cooling with ice, a solution of 774 mg (4.1 mmol) of p-toluenesulfonyl chloride (TsCl) in 3 ml of pyridine and 24 mg (0.2 mmol) of 4-(N,N-dimethylamino)pyridine (DMAP). This mixture was stirred at room temperature for 3 days. The pH of the reaction mixture was adjusted to 7 with diluted hydrochloric acid, and this reaction mixture was subjected to extraction with ether (150 ml). The resulting ether solution was washed with diluted hydrochloric acid and saturated sodium chloride aqueous solution, and then concentrated. The residue was separated and purified by column chromatography (Kieselgel 60, hexane/ethyl acetate=4/1), thereby obtaining 550 mg (yield 63%) of (2S,4R)-4-p-toluenesulfonyloxy-2-(4-methoxyphenyl)-decanenitrile.

Workup

  1. temperaturewith cooling with ice
  2. extractionthis reaction mixture was subjected to extraction with ether (150 ml)
  3. washThe resulting ether solution was washed with diluted hydrochloric acid and saturated sodium chloride aqueous solution
  4. concentrationconcentrated
  5. customThe residue was separated
  6. custompurified by column chromatography (Kieselgel 60, hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-e271945706be49ddbd2346ebdb426a18
Source dataset
uspto-grants-1991_11
Patent number
US05064564

Reaction notes

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