Sodium borohydride → 8-{2-[(2-Methoxyethoxy)carbonylamino]-6-methylbenzyloxy}-2-methylimidazo[1,2-a]pyridine-3-methanol

HRID 862553Notes

Reaction equation

HRID 862553 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]([NH:8][C:9]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:10]=1[CH2:11][O:12][C:13]1[C:14]2[N:15]([C:19]([CH:23]=[O:24])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1)=[O:7].[BH4-].[Na+]>CO>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]([NH:8][C:9]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:10]=1[CH2:11][O:12][C:13]1[C:14]2[N:15]([C:19]([CH2:23][OH:24])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1)=[O:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 196985318-{2-[(2-Methoxyethoxy)carbonylamino]-6-methylbenzyloxy}-2-methylimidazo[1,2-a]pyridine-3-carboxaldehyde

Product 1

HCID 98656638-{2-[(2-Methoxyethoxy)carbonylamino]-6-methylbenzyloxy}-2-methylimidazo[1,2-a]pyridine-3-methanolYield 72.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 3.7 g (9.3 mmol) of 8-{2-[(2-methoxyethoxy)carbonylamino]-6-methylbenzyloxy}-2-methylimidazo[1,2-a]pyridine-3-carboxaldehyde in 40 ml of methanol is treated at RT with 362 mg (9.3 mmol) of 97% sodium borohydride and stirred for 75 min. It is added to ice/water, extracted with dichloromethane and concentrated in a Rotavapor. The residual oil is crystallized using 5 ml of isopropyl alcohol, 5 ml of toluene and diisopropyl ether. 2.7 g (72.7%) of the title compound of m.p. 121°-123° C. are obtained.

Workup

  1. extractionextracted with dichloromethane
  2. concentrationconcentrated in a Rotavapor
  3. customThe residual oil is crystallized

Sources & evidence

ORD record
ord-5082e12247ab4fa393ca35242d320088
Source dataset
uspto-grants-1998_02
Patent number
US05719161

Reaction notes

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