Lithium borohydride → HCID 22645177, compound

HRID 2187951Notes

Reaction equation

HRID 2187951 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-7a11678ec1b64a87a76135f242918a11
Source dataset
uspto-grants-2002_06
Patent number
US06410538B2

Reaction notes

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