Lithium borohydride → HCID 22645199, compound

HRID 1837602Notes

Reaction equation

HRID 1837602 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][C:13]=1[C:14](OC)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]([CH:19]=[CH:18][C:13]=1[CH2:14][OH:15])[C:22]#[N:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 22645140HCID 22645140, compound

Product 1

HCID 22645199HCID 22645199, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.15 g (12.95 mmol) of methyl 2-(2-(t-butoxycarbonylamino)ethoxy)-4-cyano-benzoate was dissolved in 60 ml of tetrahydrofuran (dehydrated). 8.6 ml (17.2 mmol) of 2 M lithium borohydride was added to the obtained solution under cooling with ice, and they were stirred at room temperature overnight. The solvent was evaporated, and the residue was treated with ethyl acetate as the extracting solvent by an ordinary method to obtain the crude product, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. customThe solvent was evaporated
  3. additionthe residue was treated with ethyl acetate as the extracting solvent by an ordinary method
  4. customto obtain the crude product, which
  5. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-47c3ed99b1bb49f89bddae6c718967f5
Source dataset
uspto-grants-2004_08
Patent number
US06784191B2

Reaction notes

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