HCID 131736293, compound → HCID 131736292, compound

HRID 1053800Notes

Reaction equation

HRID 1053800 reaction equation
[Si:1]([O:8][CH:9]([CH2:30][C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=1)/[CH:10]=[CH:11]/[C@H:12]1[CH:16]=[CH:15][C:14](=[O:17])[C@@H:13]1[CH2:18][CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1>[Si:1]([O:8][CH:9]([CH2:30][C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=1)/[CH:10]=[CH:11]/[C@H:12]1[CH2:16][CH2:15][C:14](=[O:17])[C@@H:13]1[CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:28][CH:29]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 131736293HCID 131736293, compound

Product 1

HCID 131736292HCID 131736292, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-40 °C

Procedure

A solution of methyl 4-(2-((1R,2S)-2-((E)-3-((tert-butyldimethylsilyl)oxy)-4-(naphthalen-2-yl)but-1-en-1-yl)-5-oxocyclopent-3-en-1-yl)ethyl)benzoate (111 mg, 0.20 mmol) in toluene (1.6 mL) was added dropwise by cannula to a −40° C. mixture of [Ph3PCuH]6 (205 mg, 0.11 mmol) in toluene (9.8 mL), rinsing with 0.4 mL toluene. The reaction was stirred at −40° C. for 1 h and then at room temperature overnight. Saturated NH4Cl solution (20 mL) was added and the resulting mixture was extracted with ethyl acetate (3×20 mL). The combined organic solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (91 mg, 82%).

Workup

  1. washrinsing with 0.4 mL toluene
  2. customat room temperature
  3. customovernight
  4. additionSaturated NH4Cl solution (20 mL) was added
  5. extractionthe resulting mixture was extracted with ethyl acetate (3×20 mL)
  6. dry with materialThe combined organic solution was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5feafd5ba87142d4aac37021f24ef270
Source dataset
uspto-grants-2016_07
Patent number
US09394273B2

Reaction notes

Loading…