HCID 6610084, compound → HCID 11820586, compound

HRID 130618Notes

Reaction equation

HRID 130618 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:8](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:9][CH:10]=1)=[O:5])[CH3:2].CC(C)([O-])C.[K+]>C1COCC1.C(OCC)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][NH:8][C:7]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6610084HCID 6610084, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11820586HCID 11820586, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-Phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester (0.42 g, 1.13 mmol) (prepared according to the method disclosed in reference 1) and 1.0 M potassium tert-butoxide in THF (1.42 mL, 1.42 mmol) were stirred in THF at 0° C. for 30 min, then warmed to rt for 30 min. The reaction was diluted with diethyl ether, washed 1× with satd. NH4Cl, dried over MgSO4, filtered, and concentrated. Silica gel chromatography using hexanes/ethyl acetate (9:1) gave 0.195 g of title compound. (80% yield). 1H NMR (CDCl13) δ 9.14 (bs, 1H), 7.50-7.46 (m, 2H), 7.32-7.27 (m, 3H), 6.68-6.66 (t, J=2.90 Hz, 1H), 6.56-6.55 (t, J=2.90 Hz, 1H), 4.12-4.06 (q, J=7.25 Hz, 2H), 1.20-1.16 (t, J=7.25 Hz, 3H). 13C NMR (CDCl3) δ 165.8, 137.4, 132.4, 129.3, 128.8, 128.3, 128.2, 118.3, 112.1, 60.0, 14.4; MS APCI: [M+H]+=216.1.

Workup

  1. washwashed 1× with satd
  2. dry with materialNH4Cl, dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3fdaa767880b42c09c2027643dbe6b2e
Source dataset
uspto-grants-2008_06
Patent number
US07381741B2

Reaction notes

Loading…