Sodium Chloride → HCID 23154158, compound

HRID 639426Notes

Reaction equation

HRID 639426 reaction equation
[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].O=[C:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1.[BH4-].[Na+].[Cl-].[Na+]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.CO.C1(C)C=CC=CC=1>[C:2]([S:5]([NH:7][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1)=[O:6])([CH3:4])([CH3:3])[CH3:1]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 3382465Tert-ButanesulfinamideHCID 4311764Sodium borohydride

Product 1

HCID 23154158HCID 23154158, compoundYield 87.8%

Reagents, catalysts & solvents 3

HCID 76524Titanium tetraethoxideCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

2-Methyl-2-propanesulfinamide (854 mg) and titanium (IV) ethoxide (3.0 mL) were added to a toluene solution (5 mL) containing ethyl 4-ketocyclohexanecarboxylate (1.0 g) at room temperature, followed by stirring under heating for 1 hr at 70° C. The reaction mixture was cooled to room temperature and admixed with sodium borohydride (854 mg) and then methanol (5.0 mL), followed by stirring for 30 min. The reaction mixture was admixed with an aqueous saturated sodium-chloride solution, and after the resultant insoluble matter was filtered out, the organic layer was concentrated under reduced pressure. The residue was separated and purified by silica-gel column chromatography (C-300, hexane:ethyl acetate=1:2) to give the title compound (1.42 g) composed mainly of the trans isomer.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringby stirring for 30 min
  3. filtrationafter the resultant insoluble matter was filtered out
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica-gel column chromatography (C-300, hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-3c6696b6c2de4408984c1bb0dad83c60
Source dataset
uspto-grants-2010_04
Patent number
US07691860B2

Reaction notes

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