Sodium borohydride → HCID 58911260, compound

HRID 1295811Notes

Reaction equation

HRID 1295811 reaction equation
[BH4-].[Na+].C([O:5][C:6](=O)[CH:7]([N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)[N:8]1[CH2:12][CH:11]([CH2:13][CH2:14][CH3:15])[CH2:10][C:9]1=[O:16])C>CCO>[OH:5][CH2:6][CH:7]([N:8]1[CH2:12][CH:11]([CH2:13][CH2:14][CH3:15])[CH2:10][C:9]1=[O:16])[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58911279HCID 58911279, compound

Product 1

HCID 58911260HCID 58911260, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

In a 500 ml three necked flask fitted with a magnetic stirrer, under inert atmosphere, NaBH4 (1.92 g, 0.05 mol) is added by portions into a solution of imidazol-1-yl-(2-oxo-4-propyl-pyrrolidin-1-yl)-acetic acid ethyl ester a20 (9.4 g, 0.034 mol. in dry EtOH (200 ml) at 0° C. After 2.5 h, the reaction mixture is quenched carefully with a saturated solution of NH4Cl and the temperature raised up to 10° C. The solvent is evaporated to dryness and the residue is purified by chromatography on silicagel (CH2Cl2/MeOH: 95/05 (v/v)) to give 1-(2-hydroxy-1-imidazol-1-yl-ethyl)-4-propyl-pyrrolidin-2-one 39 (5.47, 68%).

Workup

  1. customat 0° C
  2. customthe reaction mixture is quenched carefully with a saturated solution of NH4Cl
  3. customThe solvent is evaporated to dryness
  4. customthe residue is purified by chromatography on silicagel (CH2Cl2/MeOH: 95/05 (v/v))

Sources & evidence

ORD record
ord-7c3de7e13d164c8bb7dd220fb0bf7e42
Source dataset
uspto-grants-2007_07
Patent number
US07244747B2

Reaction notes

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