Potassium Hydroxide → HCID 11182960, compound

HRID 1672545Notes

Reaction equation

HRID 1672545 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][C:10](=[O:13])[CH2:9][CH2:8]2.[OH-].[K+]>C(O)(C)C.C1C=CC=CC=1.C1C=CC=CC=1.Cl[Ru]Cl.Cl[Ru]Cl.N[C@H](C1C=CC=CC=1)[C@H](NS(C1C=CC(C)=CC=1)(=O)=O)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 41360218-Methoxy-2-tetralone

Product 1

HCID 11182960HCID 11182960, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 2734565N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamideCatalystHCID 10962144Benzeneruthenium(II) Chloride DimerCatalystHCID 3776IsopropanolSolvent2×

Procedure

N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-methylbenzenesulfonamide (0.333 g, 0.908 mmol) and benzene ruthenium(II) chloride dimer (0.113 g, 0.226 mmol) in 80 mL isopropanol were stirred at 80° C. for 30 minutes, then cooled to room temperature. A solution of 8-methoxy-2-tetralone (4.0 g, 23 mmol) in isopropanol (400 mL) was added, followed by potassium hydroxide (0.038M in isopropanol, 120 mL, 4.56 mmol). The reaction mixture was stirred at 50° C. for 1.5 hours, at which time the starting material had been consumed. The isopropanol was evaporated, the residue was taken up in ethyl acetate and washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica gel (15 to 30% ethyl acetate-hexane, eluant) to afford 3.0 g (74% yield) of the title compound as a fluffy off-white solid. Analytical chiral HPLC (Chiralcel OJ 4.6×25 mm, 20% isopropanol/hexane, 23° C., 0.5 mL/min) showed the isolated material to be >98% ee. 1H NMR (300 MHz, DMSO-d6) δ 7.04 (t, J=7.8 Hz, 1H), 6.68 (m, 2H), 4.72 (d, J=3.7 Hz, 1H), 3.87 (m, 1H), 3.74 (s, 3H), 2.57-2.91 (m, 3H), 2.33 (m, 1H), 1.81 (m, 1H), 1.59 (m, 1H). MS (DCI+) m/z 196 (M+NH4)+.

Workup

  1. customhad been consumed
  2. customThe isopropanol was evaporated
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (15 to 30% ethyl acetate-hexane, eluant)

Sources & evidence

ORD record
ord-5473a2030aab4f3e8316906ce50974de
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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