HCID 11220940, compound → HCID 86601650, compound

HRID 1444280Notes

Reaction equation

HRID 1444280 reaction equation
[C:1]1([C:7]2O[C:10]([C:12]([NH:14][C:15]3[CH:16]=[C:17]([CH2:21][C:22]([OH:24])=O)[CH:18]=[CH:19][CH:20]=3)=[O:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=CC=1.[CH3:25]C(C)=O.[C:29](=[O:31])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:24][CH2:22][CH2:21][C:17]1[CH:16]=[C:15]([NH:14][C:12]([C:10]2[O:31][CH:29]=[CH:25][C:9]=2[C:8]2[CH:4]=[CH:5][CH:6]=[CH:1][CH:7]=2)=[O:13])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11220940HCID 11220940, compoundHCID 18522661Acetone cardiceHCID 21226445Aluminium lithium hydride

Product 1

HCID 86601650HCID 86601650, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The carboxylic acid (10) (50 mg, 0.15 mmol) was dissolved in anhydrous THF (0.1 ml) and placed under an atmosphere of N2. The solution was cooled to −78° C. using acetone/dry ice and stirred for 10 min. LiAlH4 (1M in THF) was added dropwise (0.31 ml, 0.31 mmol) and the resulting solution was stirred for 10 min at −78° C., then allowed to warm to room temperature and stirred for a further 2 h. After cooling to 5° C. using ice/water, the reaction mixture was quenched by dropwise addition of water (1 ml) then neutralised to pH 7 with 1M NaOH and extracted with EtOAc (2×1 ml). The combined organic layers were dried (Na2SO4), filtered and the solvent removed in vacuo. The crude residue was purified by column chromatography, eluting in 60% EtOAc in heptane to give the title compound.

Workup

  1. stirringthe resulting solution was stirred for 10 min at −78° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for a further 2 h
  4. temperatureAfter cooling to 5° C.
  5. customthe reaction mixture was quenched by dropwise addition of water (1 ml)
  6. extractionextracted with EtOAc (2×1 ml)
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customThe crude residue was purified by column chromatography
  11. washeluting in 60% EtOAc in heptane

Sources & evidence

ORD record
ord-cbab3414208f4cd49c6f3cfba1e0832d
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

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