HCID 68817322, compound → HCID 68819531, compound

HRID 736776Notes

Reaction equation

HRID 736776 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:10]([N:11]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22]CC3C=CC=CC=3)=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH3:12])[CH:9]2[CH2:30][CH:6]1[CH:7]=[CH:8]2)=[O:4]>C(O)C.C(Cl)Cl.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH:10]([N:11]([S:13]([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)(=[O:15])=[O:14])[CH3:12])[CH:9]2[CH2:30][CH:6]1[CH2:7][CH2:8]2)=[O:4]

Participants

4

Reactant 1

HCID 68817322HCID 68817322, compound

Product 1

HCID 68819531HCID 68819531, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of 3-[(4-benzyloxy-benzenesulfonyl)-methyl-amino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (1.5 g, 3.51 mmol) in ethanol-CH2Cl2 (45 mL-5 mL) were added 10% Pd—C (1.12 g, 1.05 mmol) and 1,4-cycloexadiene (3.32 mL, 35.1 mmol) at room temperature. The mixture was stirred for 12 h and then filtered through celite. The organic solution was concentrated and the residue was purified by flash chromatography eluting with 40% ethyl acetate/hexanes to give 3-[(4-hydroxy-benzenesulfonyl)-methyl-amino]-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (97% yield). Mp=163-164° C. (white solid).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe organic solution was concentrated
  3. customthe residue was purified by flash chromatography
  4. washeluting with 40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d249d9aa3b264272bc5d1d024df98bd0
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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