Lithium borohydride → HCID 22645177, compound

HRID 2414428Notes

Reaction equation

HRID 2414428 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[CH:14][C:13]=1[CH2:20][CH2:21][C:22](OCC)=[O:23])=[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:17]=[C:16]([CH:15]=[CH:14][C:13]=1[CH2:20][CH2:21][CH2:22][OH:23])[C:18]#[N:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 22645154Ethyl 3-[2-(2-(t-butoxycarbonylamino)ethoxy)-4-cyanophenyl]propionate

Product 1

HCID 22645177HCID 22645177, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.1 g (3.04 mmol) of ethyl 3-[2-(2-(t-butoxycarbonylamino)ethoxy)-4-cyanophenyl]propionate was dissolved in 15 ml of tetrahydrofuran (dehydrated). 1.5 ml (2.3 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. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the obtained crude product 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. customAfter the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the obtained crude product
  4. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-2392fc39c44447939fe19f081a533ef7
Source dataset
uspto-grants-2004_11
Patent number
US06812231B2

Reaction notes

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