Sodium borohydride → HCID 68440362, compound

HRID 1712910Notes

Reaction equation

HRID 1712910 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:19]2[N:20]=[CH:21][N:22](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:23]=2)[O:12][CH2:13][C:14](OCC)=[O:15])=[CH:7][CH:6]=1)#[N:4]>C(O)C>[OH:15][CH2:14][CH2:13][O:12][CH:11]([C:19]1[NH:20][CH:21]=[N:22][CH:23]=1)[C:8]1[CH:9]=[CH:10][C:5]([C:3]#[N:4])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86626005HCID 86626005, compound

Product 1

HCID 68440362HCID 68440362, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.45 mmol of sodium borohydride are added to a solution of 1.63 mmol of ethyl [(4-cyanophenyl)-1-(trityl-1H-imidazol-4-yl)methoxy]acetate in 10 ml of ethanol at room temperature. The reaction mixture is stirred at room temperature for 16 hours and then evaporated. The residue is taken up in dichloromethane and saturated aqueous sodium bicarbonate solution, the phases are separated, and the aqueous phase is back-extracted with dichloromethane. The combined organic phases are dried with sodium sulphate and evaporated. The title compound is obtained as a white solid from the residue by flash chromatography (SiO2 60F). Rf=0.10 (ethyl acetate-heptane 1:2); Rt=7.39.

Workup

  1. customevaporated
  2. customsaturated aqueous sodium bicarbonate solution, the phases are separated
  3. extractionthe aqueous phase is back-extracted with dichloromethane
  4. dry with materialThe combined organic phases are dried with sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-ca914870585749d3903f35d179c9e520
Source dataset
uspto-grants-2010_09
Patent number
US07795253B2

Reaction notes

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