Formate → HCID 9901721, compound

HRID 2114612Notes

Reaction equation

HRID 2114612 reaction equation
[OH:1][C:2]12[CH2:8][N:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.[Li+].CC([N-]C(C)C)C.[CH2:17]([N:24]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:25](Cl)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])=O>C1COCC1>[N:5]12[CH2:8][C:2]([O:1][C:25](=[O:26])[N:24]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([CH2:7][CH2:6]1)[CH2:3][CH2:4]2

Participants

6

Reactant 4

HCID 283FormateHCID 352202Benzylphenylcarbamyl chlorideHCID 2724682Lithium diisopropylamideHCID 10011869HCID 10011869, compound

Product 1

HCID 9901721HCID 9901721, compoundYield 1.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-60 °C

Procedure

In a two necked flask under nitrogen, 3 ml of THF and 150 mg (1.33 mmoles) of 4-hydroxy-1-azabicyclo[2.2.1]heptane were placed. The suspension was cooled to −60° C. and 0.7 ml (1.46 mmoles) of LDA was added dropwise. After the addition the temperature was allowed to rise to 0° C. and was kept during two hours. A solution of 295 mg (1.20 mmoles) of benzylphenylcarbamoyl chloride in 2 ml of THF was added in 30 minutes. The reaction mixture was allowed to slowly warm to room temperature and stirred for 18 hours. The suspension was filtered and the filtrate concentrated under reduced pressure. The residue was extracted with dichloromethane and water. The organic layer was extracted with 2N HCl and the aqueous layer basified with 8N NaOH and extracted with dichloromethane. The organic layers were dried over anhydrous Na2SO4 and evaporated. The oil obtained (162 mg) was purified by HPLC-MS to obtain 4.86 mg (0.015 mmoles) 1.3% of a pure product as a formate, structure confirmed by 1H-NMR.

Workup

  1. additionAfter the addition the temperature
  2. customto rise to 0° C.
  3. temperatureto slowly warm to room temperature
  4. filtrationThe suspension was filtered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. extractionThe residue was extracted with dichloromethane and water
  7. extractionThe organic layer was extracted with 2N HCl
  8. extractionextracted with dichloromethane
  9. dry with materialThe organic layers were dried over anhydrous Na2SO4
  10. customevaporated
  11. customThe oil obtained (162 mg)
  12. customwas purified by HPLC-MS

Sources & evidence

ORD record
ord-27fa9b7f40a946ab8d4dafecde7d785a
Source dataset
uspto-grants-2008_10
Patent number
US07435742B2

Reaction notes

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