Methanol → HCID 18690685, compound

HRID 1292687Notes

Reaction equation

HRID 1292687 reaction equation
CO[C:3](=O)[CH2:4][C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[CH:8]=[N:7][CH:6]=1.[BH4-].[Na+].C[OH:23]>>[C:17]([C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:9]2[C:5]([CH:4]([OH:23])[CH3:3])=[CH:6][N:7]=[CH:8]2)=[CH:12][CH:13]=1)#[N:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 10634751[1-(4-Cyanobenzyl)-1H-imidazol-5-yl]acetic acid methyl ester

Product 1

HCID 18690685HCID 18690685, compound

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the ester from Example 1, step C, (1.50 g, 5.88 mmol), in methanol (20 ml) at 0° C., was added sodium borohydride (1.0 g, 26.3 mmol) portionwise over 5 minutes. The reaction was stirred at 0° C. for 1 hr and then at room temperature for an additional 1 hr. The reaction was quenched by the addition of sat.NH4Cl solution and the methanol was evaporated in vacuo. The residue was partitioned between EtOAc and sat NaHCO3 solution and the organic extracts dried (MgSO4), and evaporated in vacuo. The residue was purified by chromatography (SiO2, 4 to 10% methanol in methylene chloride, gradient elution) to afford the title compound as a solid.

Workup

  1. waitat room temperature for an additional 1 hr
  2. customThe reaction was quenched by the addition
  3. customNH4Cl solution and the methanol was evaporated in vacuo
  4. customThe residue was partitioned between EtOAc
  5. dry with materialthe organic extracts dried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by chromatography (SiO2, 4 to 10% methanol in methylene chloride, gradient elution)

Sources & evidence

ORD record
ord-f5a744a2603e4b41908c2d81bf39f3d6
Source dataset
uspto-grants-1998_05
Patent number
US05756528

Reaction notes

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