Cyclohexanecarboxaldehyde → HCID 11138490, compound

HRID 1525291Notes

Reaction equation

HRID 1525291 reaction equation
[CH:1]1([CH:7]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][C:10]([S@:13]([NH2:15])=[O:14])([CH3:12])[CH3:11].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>ClCCl.[O-]S([O-])(=O)=O.[Cu+2]>[CH:1]1(/[CH:7]=[N:15]/[S@@:13]([C:10]([CH3:12])([CH3:11])[CH3:9])=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 11138490HCID 11138490, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
37 °C

Procedure

Cyclohexanecarbaldehyde, 26-a, (13.58 g, 0.121 mol) in dichloromethane (250 mL) were added (R)-2-methylpropane-2-sulfinamide (17.6 g, 0.145 mol), PPTS (3.03 g, 0.0121 mmol) and anhydrous CuSO4 (58 g, 0.363 mol). The resulting mixture was stirred at 37° C. overnight. The mixture was then filtrated and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate=5/1) to provide the product, 26-b, (23 g, 88%).

Workup

  1. filtrationThe mixture was then filtrated
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-efe8254a35ab43498aa0f765de184527
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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