HCID 53890816, compound → HCID 19600230, compound

HRID 611414Notes

Reaction equation

HRID 611414 reaction equation
[C:1]1([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:15][CH2:14][C:13]3[O:16][CH:17]=[CH:18][C:12]=3[CH2:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1>C1(C)C(CCO)=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[CH2:19]([C:1]1[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH2:15][CH2:14][C:13]3[O:16][CH:17]=[CH:18][C:12]=3[CH2:11]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1)[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 53890816HCID 53890816, compound

Product 1

HCID 19600230HCID 19600230, compound

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 882672-Methylphenethyl alcoholSolvent

Procedure

A solution of the above 5-(stilbene-4-sulfonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 20 ml of toluene-ethanol (5:1) was hydrogenated at room temperature at atmospheric pressure over 49 mg (0.053 mmol) of chlorotris(triphenylphosphine)rhodium (I) until the starting material disappeared on TLC. After the reaction mixture was concentrated under reduced pressure, the resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1) and crystallized from diethyl ether-hexane to yield the desired product.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. customthe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1)
  3. customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-a75ab4a2709a444a9db06481adc7fa49
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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