Sodium borohydride → 3-Hydroxymethyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine

HRID 1195726Notes

Reaction equation

HRID 1195726 reaction equation
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][C@@H:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15][C@H:14]3[OH:22])[C:6]2=[N:5][C:4]=1[CH3:23])=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][C@@H:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15][C@H:14]3[OH:22])[C:6]2=[N:5][C:4]=1[CH3:23]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 228438253-Formyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine

Product 1

HCID 228438393-Hydroxymethyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g of 3-formyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine is dissolved in 150 ml methanol, and excess sodium boro hydride is added in small portions at room temperature. After reduction has been completed, 150 ml icewater is added. The volatile components are evaporated in the rotary evaporator in vacuo. Subsequently extraction is carried out 3×with 40 ml ethyl acetate each time. The combined extracts are stripped off in vacuo of solvents, and the crystalline residue is recrystallized from methanol. The title compound of 192°-193° C. is obtained.

Workup

  1. addition150 ml icewater is added
  2. customThe volatile components are evaporated in the rotary evaporator in vacuo
  3. extractionSubsequently extraction
  4. customthe crystalline residue is recrystallized from methanol

Sources & evidence

ORD record
ord-08b224fb8b06463da23e30973a23365f
Source dataset
uspto-grants-1992_05
Patent number
US05112834

Reaction notes

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